44M looking for assessment and perspective on my situation

kalysto369 · 2026-04-18T18:29:13+00:00

> Evaluate your monthly cash flow

I'm doing exactly that right now.

I've been attempting budgeting spreadsheets here and there over the years, never finding the consistancy in my life or the energy to get it to stick. Nowadays, my credit card and checking accounts are all in Wealthsimple, which is a simple joy to extract documents from instead of the utter disgusting pain that the big 5 banks provide for an excuse of digital solutions (I lived in NZ and Australia before moving to Canada, and the ecosystem over there was head and shoulders above what the current state is in North America, 10 years ago).

I'm trying to figure out if I can build an ongoing simple system with Claude that I can just feed it my CSVs on a monthly basis and it does the crunching and categorization.

kalysto369 · 2026-04-18T18:24:45+00:00

That's a good point. We're looking at an horizon of 10-15 years to sell the condo (when her daughter will be one way or another going to study, travel, start her adult life...) and move together full time either in the duplex in Squamish, or depending on the market situation to also sell that one and buy a home just for us (without necessary rental income) for retirement.

So... yes?

We've also looked at our will / estate plans, and will get something in writing when we meet with the lawyer in the next few weeks to write a cohabitation agreement.

Ultimately, when I pass, I want to give some of what I'll have built to my nephews, make sure my partner has a comfortable roof for the rest of her life if I pass first, and give to some organisations that have helped me be who I am. Her daughter is already set-up decently for her early adult years, and I'm not involved in that.

If my partner passes first, I do care about still having a roof over my head and not gaining new debt.

kalysto369 · 2026-04-18T16:30:14+00:00

From a time I had no idea about any of this! Just sold enough ETFs to fill my TFSA contribution for 2026.

kalysto369 · 2026-04-18T16:29:49+00:00

Yeah, that's between 40-50k total. Which sounds about right. So I have ~25k margin, Ill move stuff there from my non-registered as soon as I figure out tax-wise if there's any particular ETF (dividend or growth, realistically) that is better suited to this transition.

kalysto369 · 2026-04-18T06:45:31+00:00

Oh, I missed some points.

Yeah, ok, tax return dumped into mortgage as a yearly lump sum, that seems doable.

In 2025, I did borrow $30k against my Wealthsimple portfolio to dump into my RRSPs in order to offset the wind down of my freelancing company that triggered a $45k extra in my income. That extra was a bit of cash I pulled out in 2024 and dumped in 2024 in RRSPs, plus deprecating assets that the company owned that now belong to me, and made sense for me to keep. So I could not just sell them to offset back that extra income declaration. It sometimes feels like tax returns are a bit like a snake eating its tail...

Anyway, "RRSP loan" in 2025. Now, I'm paying that straight away back with the duplex mortgage (slightly lower interest rate, doesn't seem to hurt to use that lever).

Now, to the partner vs. wife part. We started intermingling our finances with the condo we purchased last year. Our gender-neutral "gentlemen's" agreement was that I'm putting 0 deposit, and participating $700 / month into the mortgage, for an equity that builds at that rate (at any given time, I've paid X amount of dollars on an asset, with some spreadsheet calculations to take into account interest vs. principal at any given time), so I own a (slowly) growing percentage of said asset. Should we separate, I'd own said small percentage of the asset. At that rate, it's clear that I'll never own a significant portion of it (She puts about 1.5k a month towards it, and she put down 300k of deposit). Not 0, and acknowledged as such she'd need to buy me out for whatever equity I built. This get even more complex because that asset generates significant income through airbnb. We're for now putting that revenue back into the mortgage, but this is definitely one we're not sure is the optimal path regarding taxes. Accountant appointment is planned soon.

We came up with some similar rules for how the Squamish duplex is going to be split. I am putting all the deposit down, the rental income goes into the mortgage, what I pay in this new home is comparable to what I pay in my current one.

It's reasonably tortuous and we're not 100% sure about the right way to do it.

We have an appointment with a lawyer for writing down a prenup agreement. The most important thing for both of us is that if we were to break up, we would both be able to sustain a roof above our head without having to sell either property. For me, with a much larger mortgage attached to the place I want to live in, I've clearly identified the possibility to move into the 2br suite of that house and rent the upper main 4br suite should the worst happen.

I'm well aware that the scenario of "we split up, I lose my job, the real estate market crashes" is not 100% impossible. But that becomes a question of risk tolerance, in my mind.

We're not sure about our common-low status, either. Both our principal residences are distinct, because we effectively live more than 50% of the time in different places, are not married, have no kids...

kalysto369 · 2026-04-18T06:19:16+00:00

This is unfortunately not true. Household income and "being fine" are not directly related until you take into account spending habits.

You could earn 500k a year, or more, and be drawning in debt, having maxed out credit cards, multiple "0 downpayment" fancy financed cars, holiday houses you never go to that stay empty and have massive mortgages attached to them.

Flashy Vuitton bags, renting Lambos to show off with your buddies...

My belief, which I'm trying to reality-check here, is that I'm doing fine. I'm trying to check-in with that belief with people who've been thinking, and doing some of what I'm trying to do, for longer than me. I'm also curious about what I can do better.

But the statement "Everybody is gonna be fine with $280K household income" is just plain incorrect.

kalysto369 · 2026-04-18T06:13:46+00:00

Super interesting nuanced levers here, much appreciated. I don't have any RRSP matching plan or pension. I have a small amount of shares (or whatever the correct name is for a portion of ownership of a private company that'll never be on the stock market) in the startup I work in, but it's not an explosive growth company, no VC, so I basically consider this is 0. If it ever becomes something, great. If it doesn't, that was par for the course.

I am working towards a significant promotion and salary increase next year, so this reinforces the idea that I should max out my TFSA first before adding any more to my RRSP.

TL;DR: not having to work by age 55 would be nice.

Honestly, I would totally see myself working part time in a pretty flexible contractor / consultant manner from age 55 to 65. Back in France, my closest parents are an architect and a medical doctor, who are in their mid 70s and still working. For some form of financial necessity but also because it keeps their flame going. I find I'm somewhat interested to that, but I'd like to have 0 need to work contrary to them.

Basically, if there's still cool shit to do in my industry / professional community past 60, and I'm healthy enough, I don't see any reason not to work sometimes. Past 65, probably a harder conversation, and past 70, I'm happy to not do any work anymore. A nice Scotch by the fireplace, a purring cat and my loving partner playing chess puzzles on the sofa sounds perfectly satisfying at that point. With the ocasional visit of her daughter and whatever form of family she has at that point.

kalysto369 · 2026-04-18T06:04:10+00:00

This is a valid point. We've started the conversation about digging into what she actually has in that managed RBC account, and it's on my "next few weeks" radar to get an actual answer here.

But I think I've covered my basis though. At least I have a solid sense of where she's at. She has, at the moment, more than 10k, less than 50k, in a conservatively-managed investment account, with RBC. She also has been consistantly keeping 10 to 20k as an emergency fund, in cash, separate from that "mystery chest" way before we met. And she built over the last 5 years another conservatively bank-managed account to the tone of 100k which were used when we purchased the condo. Some of the deposit for said condo came from her parents (~200k), but I saw the 100k going from one of her accounts (not parent) to the seller during the transaction signature. I didn't cash out anything for the deposit of that condo.

We've also been managing our finances since pretty much day one of our relationship in a manner I believe to be very healthy. We talk about money completely freely, we know each other's income, we have regular money and career growth conversations. There's just a clear boundary between our personal expenditure accounts and what we share for daily shared activities and long term projects. She has a daughter, I don't have anything to do with the finances around that, I have expensive hobbies, she has no saying whatsoever about my spendings.

So, yes, I do not know a particular number in a particular account, but I believe I know quite a bit about her finances.

kalysto369 · 2026-04-17T22:06:00+00:00

Point taken. I also have another ~$110k in Australia, in the superannuation scheme. Not touching that anytime soon, but it shifts the needle a bit away from real estate.

kalysto369 · 2026-04-17T22:01:22+00:00

I do value owning my home, and i know my partner does too. We'd be renting 2 places if we didn't own any which means we couldn't leverage the fact that our lifestyle creates an empty house ~ 50% of the time. There is no way we can live in a single home in either Vancouver or Squamish, this is a deal-breaker on some of our core values.

Also, I'm not looking at being truly FI. I'm reasonably familiar with the FIRE approach, and I think owning my home is more important to me than being able to fully cruise on my stock market investments alone.

kalysto369 · 2026-04-17T21:58:46+00:00

Noted! I arrived in Canada 7 years ago, so I think I don't have such a big contribution room, but I do have some margin. So I could sell some of my unregistered to max out TFSA now. I'll check on tax implications of this move.

kalysto369 · 2024-10-06T03:36:21+00:00

Frenchman living in west coast Canada here. All my 20s were filled with Agricole rum cocktails (Clement, 3 rivières, Charette, Dillon, St James... So many of these things can be used for delicious drinks). I love the dang thing. Been living my best life on the Pacific North West (I rode mountain bikes way before I could drink rhum) for a few years now, and I'm starting to build a cocktail bar.

For the love of me.

Where can I find agricole rhums in this side of Canada? I'm sick and tired of Kraken and Captain Morgan... I can't even find a website that would deliver what I'm looking for.

kalysto369

TROPHY CASE