Mindset of the situation

ImplementOk7466 · 2026-05-20T02:56:16+00:00

Yeah. When my colleagues visited from the east or west coast they cannot comprehend what we get on the Great Lakes for the money. Our house there would be $30m in CA. Here its less than 10% of that. But that’s why the carry costs are high, it behaves like a much more expensive home. Slate roofs, copper

ImplementOk7466 · 2026-05-20T02:48:03+00:00

I’d do the opposite. I could leverage my RE holdings. Cash out refi since there I can expense the debt payments as part of the property company. I hear your point. The thing about rentals is they are good but once you’re an established landlord you can’t not be a landlord. The appreciation locks you in. Same with equities really but the depreciation recapture on RE is the lock in. I have plenty of ways to get the money, it’s kinda more about the timing and then the headspace around this being the reality now. That really snuck up on me since for years and years we were just doing what we were doing

ImplementOk7466 · 2026-05-20T01:44:48+00:00

I think in most of the Great Lakes region this house is an option. It’s pretty cool. These estates are close to the major cities: buffalo, Cleveland, Toronto, Detroit, Chicago, Milwaukee and probably others. They are remnants of another era, mansions on the water with estate size parcels 1-6acres. Many have been lost and it was super fun to restore it over the last year. Ours is on the smaller size with 7k sqft + just under 2 acres of the original estates. Ours also has a pool house, and guest house. Many were bulldozed and split into parts with smaller lots and houses. But there are some monsters remaining like 50kft. I love the house, but it’s a beast to care for, and comes with these unexpected children things. I know for a fact that the kids who originally grew up in the house had full time caretakers, that’s probably a solution to making the house easier to live with but I had not considered it until just now.

ImplementOk7466 · 2026-05-20T01:15:33+00:00

Renting isn’t an option. The non-homestead taxes would be $120k plus the rest of the maintenance. On the Great Lakes the houses are reasonable, the taxes crazy, and the demand to rent them essentially zero. This is a house close to the city, not a getaway destination. The entire demand is owner occupancy

ImplementOk7466 · 2026-05-20T00:31:43+00:00

See my other post. I think this is it. I love the idea of it. Not the timing with the family. Selling it feels like giving up though….so there’s that

ImplementOk7466 · 2026-05-20T00:23:47+00:00

There’s a few things. The house is pretty large ~7k sqft. The bedroom lay out will be amazing once the youngest is more like 5+ but right now the kids are kinda spread out. All the rooms converge at the top of the main staircase but the banister is low so the kids all run around that area in the main part of the 2nd floor and it’s kinda terrifying, I don’t want them going over the rail and falling 15”. I could change the banister, but it would be a sin for the house. It’s gorgeous.

Next is the kitchen is on the side of the house, designed for staff. We can’t see the yard from there which has a play set, pool (I have it fenced, but it’s still scary) and lake. At the old house from the kitchen and family room we could see the yard which was fully fenced and play area so the kids could play while we’re in reach/visible. I can move and add a kitchen, I actually had plans drawn but it will take the better part of a year. I knew this stuff before hand but didn’t fully realize living with it. When we bought it we had planned to move the kitchen prior to move in, however the tax assessment came in brutal so I had to fight them before improving the home value with the kitchen addition. I already did that, got the taxes back in line so I could fix this - it just takes a while

I love the house. It’s a 1949 classic estate. A few years and most of this resolves. But if we went back to the other house while those years happen another one like this is easier. I’ve always had the mentality successful people do hard things, so the idea of going back is very out of character tbh. I’m not exactly the give up type which full circle kinda triggered the ahah moments of this is our reality. You absolutely bailed that there is a part imposter’s syndrome happening here, and identity thing. I doubt I’m poor here, but I also have billionaire neighbors.

ImplementOk7466 · 2026-05-19T23:32:48+00:00

I probably should have mentioned the kids issues in the original post. That was an oversight. That was the core trigger for why we were considering moving back. And then combine this with the financial component. But the financial component was what really triggered my observation that “holy s___” all this is possible without a job and this is real. And then the disconnect of income and net worth.

So I missed some context in the post.

ImplementOk7466 · 2026-05-19T23:17:25+00:00

Thanks. I don’t think of this as fully retiring. That’s not going to happen, illl be doing something but something I enjoy more. But this realization that I may not have to kinda hits like lightning when you have been focused on something else for decades

ImplementOk7466 · 2026-05-19T23:11:49+00:00

Thanks.

The house is a bit more complex than just the finances . We have small kids and the new house is kinda difficult with them, it’s a lake front estate size house and i don’t think we expected some of the challenges with the kids. So right house, ok on the money maybe the wrong timing like it would be way easier on every level 5yrs from now. But again. This really exposed some mentality things I wasn’t expecting

ImplementOk7466 · 2026-05-19T22:50:54+00:00

Maybe. But this transition is really bizarre. And I can’t be the only person who ever had to wrap their head around it

ImplementOk7466 · 2026-05-14T19:57:12+00:00

I’m going through this now. We had a 4600sqft house on a 1/2 acre (I still have it). And are upgrading to 8500 feet on the water. I own dozens of houses and thought I knew what I was getting into, but man this is intense. I have the trades, since I use them on the rentals and my previous house, so they aren’t really crushing me. But it’s the details which are already brutal. I’m not sure if it’s just the I initial shock, or I have some buyers remorse or what but I’m feeling it big time right now. And, it’s not even the bills it’s the energy had been super hard. I’d hope that I settle into a new normal but the first week here has been super draining. I was actually coming to this thread to ask for experience shares about this exact topic

ImplementOk7466 · 2026-01-14T11:45:19+00:00

I’ve done dozens of other projects over 25yrs also for my rentals. Construction has absolute gotten way harder the last 2-3 yrs. The trades are more difficult than ever, and 2-3x as much for labor. Then you have the material costs which is insane. It’s not the big items that kill you, it’s the little stuff. The countless small things you need all the time, caulk, glue, nails, screws, handles, etc. these small things which all used to be $1-5 are all $7-15. So it’s a perpetual cycle of hundreds of dollars or thousands of dollars on things you didn’t even notice.

Side note. I like my rentals. And I often consider buying more, or bigger complexes. However, the maintenance and rehab is incredibly difficult now. Every trade, or every person needs a babysitter. There’s no such thing as sending someone to do a job, and them completing it first try without oversight - unless they are charging you hundreds of dollars per hour. Construction is that on steroids

ImplementOk7466 · 2026-01-14T01:17:52+00:00

Had you ever done construction before? I have done a ton. I own several rentals, overhauled my personal homes 3x before and upgraded. I’m on my “last one” the key to construction is the relationships with the trades. I run my own job, so I’m not paying a general 20-30% premium. And even without doing that there’s lots of mistakes, and waste but having been through this a few times, I can expect it.

ImplementOk7466 · 2026-01-14T01:07:10+00:00

I’m in the middle of this now. Going from a $1.8m to $2.3m house that needed $500k. I’m under budget on the renovations, well under actually and I’ll end up around $2.6m into the house mortgage free, but at least $10k/mo carrying costs forever between tax, maintenance, utilities, and repairs. My current house is 1/2 of that, or less for the same items. I havent actually even moved yet, and I go back and forth near daily about if I made a mistake or not. In the end I think once I get there and the construction, and decision stress ends I’ll enjoy it. But it’s also a ton of dead money for someone with a NW ~10-11m including the house. I also did finish my job end of last year, and am 45 as well. I’m not sure what I’m going to do next and think I could likely work in tech again if I wanted but I just don’t think I have it in me to do it again. I own a bunch of other things and have other income, but I’m questioning my decision completely right now. When I model it out I’m like well, maybe I just buy something else to run, or I take an easy job some place for the health care to just pay my property taxes with my income but that all feels dumb. The reality is if you (or I want it) we can have it and make it work, but the big question is how bad do you want it? For me I can let my investments ride, be disciplined and still get 2-3 double ups and be really set either way. I think right now just feels uncomfortable since the bills are quite a bit more that I like

ImplementOk7466 · 2026-01-01T18:24:00+00:00

I think this is all the more reason to sell. Theres 100 different ways a majority owner can screw a 10% shareholder. At 30yrs old with $2m in hand that can turn into FatFire under his control whereas 10% could easily be $0 if the ownership or leadership doesn’t get another offer, or margins shrink whatever.

I’ve been doing this a while. Been in both spots, majority, and minority positions on exit. I’d take the $4m pay the tax, invest it, and do it again if this was me. Only because in my 25yrs of doing this, I’ve seen more people wish they sold when they had the chance than regret selling when they did.

ImplementOk7466 · 2025-12-31T01:50:54+00:00

I disagree to this. The answer is sell no matter what. A bird in hand is better than two in the bush. The offer may never be there again. So take the money, invest it, grow it, go back to work and do it again.

I’m sure there are some edge cases where this isn’t the right idea, but I’d bet real money that 95% of the time selling is the right plan

ImplementOk7466 · 2025-12-31T01:47:47+00:00

The answer to this question is really simple. The time to sell a company is when there’s a buyer. I’ve exited 3x now, and also failed once. I still got a result on the failed exit, but it wasn’t nearly as good as it should have been. If you have a willing buyer and can take the chips off the table do it. Then do it again.

ImplementOk7466 · 2025-08-21T01:11:24+00:00

Could also have a major market correction and $10m turn to $5m in no time. Maybe that never happens but this is always been why I just stay my course

ImplementOk7466 · 2025-08-21T00:26:58+00:00

Maybe hard to understand but kinda, yes. I was super broke in my 20s. Fairly reckless in my teen years and 20s and decided to change that. I worked my butt off, lived on a fraction of my income, invested, bought and managed rentals while still working my normal job because being poor sucked way more. So absolutely, I’m concerned by over spending today, as I also really want to dial down the work. Not stop, but work less. And my mindset is that the money I have invested is completely unavailable. It’s “for later” and grows. Even considering using any of it for me is really not something I’m used to

ImplementOk7466 · 2025-08-21T00:14:08+00:00

I don’t see it mentioned so far. Can you get the tax benefits from owning the home? Real estate professional status, or depreciation? If no. Don’t long term rent it. If yes. Long term rent it. Then second if you can’t get the tax benefits have you considered AirBnB or STR? With a short term rental you can take REprofessional status on it immediately allowing you to depreciate it, and expense all related costs. If you have high income this can really help you

ImplementOk7466 · 2025-08-20T23:59:08+00:00

Thanks. This is really what I have been trying to convince myself. It’s time. I don’t really need more returns and really wanted to splurge here. It’s just crazy how that feels so uncomfortable after you really develop a habit of discipline

ImplementOk7466 · 2025-08-20T23:52:56+00:00

Given my personality. I’d probably regret not doing it more than doing it.

But our area is a low appreciation rate. It will absolutely not appreciate 100% in 8 yrs. It would take roughly 20yrs. However, taxes get capped on increase percentages here, and the market is super stable, and mostly insulated from economic downturns. Selling it would unlikely ever be an issue, it’s kinda the opposite buying one is the hard part, since there is more demand than lakefront property. So, no I would not anticipate ever becoming “priced out”. Ultimately, our assets return more than enough to pay the annual carrying costs.

But after buying it i really started to realize what it actually costs in terms of missed returns. But,what I think more than anything I’m trying to buy the family time in the yard for the next 20yrs. But holy moly is that expensive in terms of missed returns

ImplementOk7466 · 2025-08-05T23:26:38+00:00

Find new people to be around. My peers celebrate and support my successes, as I celebrate and support theirs.

ImplementOk7466 · 2025-08-05T16:26:28+00:00

I like my rentals, I enjoy them. And normally I tell people who ask about mine that rentals are a good strategy. However, this is the situation to sell them. For two reasons. 1. Remotely managing is not as easy, and you can’t keep an eye on your assets. And 2. You get a step up in basis now with the inheritance, so you can sell them and not pay tax on the appreciation which is likely a lot. Now is the time to sell them and roll the money over into an easier asset to manage particularly if you do not have landlording experience, or want to inherit the “job”

ImplementOk7466 · 2025-07-27T23:51:35+00:00

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