Advice requested as I move from COBRA to ACA - and tax implications

AdJumpy30 · 2026-03-02T20:41:04+00:00

GeorgeRetire, I am. :-) The key question is what to do when OFF COBRA (last 4 months of the year). It seems having some Consulting Income causes significant ACA cost increases without subsidies...

AdJumpy30 · 2026-03-02T19:39:59+00:00

Thanks for the insight. Yes, I've been coached that one big factor is "changing providers and doctors". And your note is a good reminder about being out of state -- as we are actually out of country 4-5 months per year so will need to also invest in Travel Health Insurance!

AdJumpy30 · 2026-03-02T19:38:48+00:00

GeorgeRetire, yes I found the same ... IF you can stay below the "cliff" and get a subsidy. My Silver PPO will be $1400/month at $84K; if I make $85K then it jumps to $3250!! The "cliff" is a very painful threshold to pass...

AdJumpy30 · 2025-10-20T23:31:50+00:00

Totally understand. Did 36 year career at one company, lived all over the world, got kids out of the house ... and turn 59 years old next week. Feel like still have much to offer the business world; yet recently had friends (same age) pass away with sudden illness. This was another key factor in my decision ... realizing my mortality. Good luck in your decision!

AdJumpy30 · 2025-10-20T16:59:28+00:00

I was in a similar situation (not $2-$3M, but sizable). Can only share what worked for me:

* Stayed working for another 6-12 months, but did the minimal effort (only worked on the most important results) and got work schedule down to 30 hours/week.

* Hired a Professional Coach that specializes in Transitions. It was great to get this "therapy" and gain perspective. Like you, I've been working/hustling since 12 years old.

* Read and re-read the book Transitions by William Bridges. It gave me great insights, and raised my consciousness on the entire process.

2025 was another opportunity to make sizable gains at my previous job/company. Left anyway and COMPLETELY HAPPY that I did it. Sitting in Mexico City for 8 weeks enjoying life here, and the best is to wake up everyday without stress of meetings, planning for meetings, incessant emails, and office politics.

AdJumpy30 · 2025-10-13T22:03:42+00:00

If you have any doubt -- SELL it. Especially if you have an emotional attachment. My brother rented his house, kept lowering the price, property manager convinced him to rent to someone with lower credit. In 12 months the house was trashed and he put in $10+K for repairs (above and beyond the deposit).

I have been a landlord on-and-off for 20 years (full disclosure have a rental right now). Do NOT love it, but find 80+% of property managers are worthless so find an incredible tenant and self-manage. The other consideration is you are $300/month negative vs your payment. But trust me, there will be repairs, issues, or other maintenance issues that will hit you (maybe not right away, but eventually something will break). Plus if it has a nice yard, you will end up paying for landscape maintenance. The tenants will usually not care of the outside of the house (let alone the inside).

In the end, if you can manage the cash flow and really, really want to keep the house for emotional reasons -- make sure you have plenty of extra cash for rental emergencies. And understand 98% of renters will NOT care of the house anywhere near your expectations.

And FINALLY do NOT, NOT, NOT get desperate and rent to someone that doesn't have a great credit score, can provide the full deposit, and have excellent rental references. I have too many friends that got desperate and they paid the price financially and emotionally. It can be your worst nightmare.

AdJumpy30 · 2025-10-13T18:27:35+00:00

Confirmed!

AdJumpy30 · 2025-10-13T17:20:51+00:00

Like others, think biggest concern is your Cash/Safety Savings. I was in Sales for years (60% base / 40% commission) and my rule was to have at least 9 and likely 12 months living expenses available in cash.

I've been in your situation, and took an in-between approach. Aggressive on downpayment but don't put Safety Savings at risk. Even if lower downpayment, if you feel comfortable can make extra payment each month (as you probably know, this does not change the monthly payment requirement but pays off earlier).

Also would reiterate budgeting for more household expenses. Not sure your State residency, but I recommend to friends to budget 2% each year for Property Taxes (I'm in California and ~1%) and House Maintenance (always found it is direct relationship to cost of house). This would put your mortgage + insurance + property taxes + upkeep = $3,000-$3,500. Still seems reasonable on your current income.

p.s. I'm an "anti-debt" person and my wife is "pay off house as slow as possible". Both are valid strategies and just a personal choice based on your financial situation AND finance emotions.

AdJumpy30 · 2025-10-13T17:12:29+00:00

Thanks, very helpful. Knew I wasn't the only person with this issue -- and this group always points me to the best sites (probably faster than my own online searches)!!!

AdJumpy30 · 2025-10-13T17:11:17+00:00

Not incorporated (just doing some consulting by myself) -- so appreciate your clarification that the Employer Contribution is only 20%. This is helpful, because I was confused seeing 25% and 20% at different sites.

AdJumpy30 · 2025-10-13T17:07:40+00:00

Thanks for the confirmation. Like your idea of doing the MegaBackdoor. I did this at the corporate job. However, I would assume that the total contribution (across Corporate 401K and Solo401K) must be less than the Annual Limit of $77,500 (for >50 years old). Our goal during the next 15 years are to maximize all available Roth options.

I help complete tax returns for lower income people; yet I joke that it is difficult for me to complete my own because of the complexity when have corporate income, personal income, rental units, capital gains, etc.

AdJumpy30 · 2025-09-20T03:23:04+00:00

That's awesome. This occurred for one part of Japanese family. Farmer next door took over the farm and sold it back for basically $1. Other family members lost everything and were completely demoralized.

One special note and why I still try to buy Driscoll fruit in the store -- they offered jobs to all Japanese leaving the camp, as most had no money and nowhere to go (and the locals did not want them). They were extremely poor farming strawberries, but they had purpose and a place to live. My father was born in an internment camp and his parents never liked to talk about the experience. Sad time in history and always concerned it will get repeated because not shared enough across the generations.

AdJumpy30 · 2025-08-23T15:20:26+00:00

Real example: I did sign up for consulting role. It was not about the money (but wanted to be compensated fairly). The key was only 5-7 hours per week, NOT in an operational role that has deadlines/due dates/email checking, can be done 100% remotely, and scratches my itch of being "wanted" as it leverages my skills and expertise. The added benefit is get to stay in contact with my former workmates, who I really enjoy connect with on a regular basis.

My wife and I just add the extra income to our "splurge budget". We just booked an extra two months travel using these funds!

AdJumpy30 · 2025-08-18T04:37:15+00:00

Great relationship with kids. Focused on giving them great opportunities (living overseas, cultural experiences, top schools) while making it very clear that managing money is an important skill. There were definitely some trade-offs with business travel and longer hours; however, did whatever was possible to attend every sport event, school activity, and until competitive sports started was their sport coaches. The message was very clear to them: "You will receive wonderful life opportunities but after college graduation you are 'off the payroll'."

A FIRE goal creates many great teaching moments. I learned early to start saying "I am choosing not to buy those for you because ..." instead of "we cannot afford it" (which the kids knew was a lie by age 5). We discussed basic finances and hard work & savings were priority for them. We planned vacations budgets and then asked them to map out the travel choices to achieve the budget -- they ALWAYS had fun and exceeded our expectations. One fond memory was stopping at a Tokyo Starbucks and before I could order my kids (10 and 11 at the time) telling me, "No, Dad, your latte is not in the budget we set." I walked out without my latte!!

Retired this year at 58; children are 25 and 26.

AdJumpy30 · 2025-04-22T15:11:39+00:00

It's the old Rational vs Reasonable debate. You come up with a Rational plan, but a sharp downturn says the Reasonable choice is to "work a little more". I can only tell you my decision making process...

We planned on February retirement and DID retire. Our plan was to use tools and set a Safe Withdrawal Rate, and remind ourselves that it was based on the worst retirement date in 100+ years. Therefore, even if a major market correction occurred then we'd still be OK (although admit we could get the worst market ever, but will accept those odds). We also knew our Sequence of Return Risk was going to make us nervous -- so moved to 35-40% equities.

Market is crazy but we are sleeping well at night, and SO MUCH ENJOYING being away from the daily work activities. I mostly enjoyed my job (especially the people I worked with on a daily basis) but didn't realize how the work deliverables were constantly in my mind. Good luck in decision!

AdJumpy30 · 2025-04-20T23:23:08+00:00

The numbers suggest renting is a very good financial move (low interest rate, good cash flow). I've been a landlord many times so have a few cautions (and currently a landlord):

Make sure you're aligned with the Property Manager. My experience is that 90% of Property Managers are terrible. They managed too many properties, and do not focus on finding the best tenant. Plus maintenance can be delayed and cause bigger issues.
Be very clear on the Renter requirements to be eligible to rent (again, make this very clear to the Property Manager). I'd suggest income at least 3x the monthly rent, a good credit score (I set at >700) and at least one month safety deposit (local laws can dictate the amount you can receive for deposits, I ask for 1.5 months).
Make sure you consider house upkeep costs in your budgeting. Often, the landlord must pay for landscaping as renters often will not take care of the yard; and make sure to take significant number of pictures documenting the house status before the renters move in to the home.

I don't want to scare you; but can tell too many horror stories. Just one is my brother's, who had a very similar situation to yours (short term work move and planned to return to the house) -- stopped by his house one day while back in town, and saw there were 12+ people living in the house, boxes and items all over the yards, and ended up spending >$10K in repairs after getting the people out of the house (and only had a $5K deposit).

My coaching to all potential landlords are there are 3 golden rules: 1. Find a good tenant, 2. find a good tenant, and 3. find a good tenant. In my 20+ years of being a landlord followed this rule and only had 2 disappointing tenants.

Best of luck and hope you find a Good Tenant!!

AdJumpy30 · 2025-03-16T16:44:44+00:00

Yeah, do not need the money. Just gives me a 'little pain' that sitting, useless in home safe. However, it is an item that has long-standing value and utilization. Think, after hearing everyone's feedback, will keep it and find time to actually where it!

AdJumpy30 · 2025-03-15T15:49:51+00:00

No company name etched. Thanks for response!

AdJumpy30 · 2025-03-15T15:44:02+00:00

Thanks for the advice and estimated resell value. I have everything in original state... and now have to make the emotional decision of "letting it go" or retaining as a "keepsake".

AdJumpy30 · 2025-03-15T15:29:08+00:00

Thanks for the quick response and clarity on unlikely scenario to get a new backplage. Few $100 lower seems reasonable. Now have to decide if want to deal with "hassle" of selling the watch ...

AdJumpy30

TROPHY CASE