When you start thinking in terms of ROI on happiness, some choices become pretty natural. Even more so if you convert dollars to time spent sitting in your chair at work, even more so when it's compounded at 4-8% yearly.

In other words, at some point I started to think how much time I'll have to spend at work for a nice car, thus I drive a 3000$ used Kia that's in good shape with low mileage. Am I any less happy? Maybe 0.5% less than if I had a cooler car, but I'll be spending probably 2-3 years less at work so that's good ROI.

Start doing that for a bit and you've got most of the work done. That doesn't mean being a cheapskate. I don't care how much my daughter's gymnastics class costs, that's good ROI. Having a nice logo on my shirt gives me jack squat so no money there. I'm trying to push off on the whole family Disney trip because I'm sure it's great memories but I'm pretty sure we can juice more happiness out of the little fortune that would cost.

Also, not just taking for granted that you have to pay for stuff because that's how it is. The 3000$ car is only insured for liability. If I crash it and I'm still alive I'll buy another one cash.

Living below your means is freedom. My girlfriend was able to not work a whole year to stay with our second born because we lived off one salary. That cost me a few 10Ks out of pocket. No problem. I'm penny pinching where it doesn't matter so I can spend where it does.

I have a number in mind I can probably reach within 4 years (I'm 40), then I just won't have to worry about the money coming in, but I'll still want to work at projects, jobs (though not full time), independently of how much money they bring in (though I'd like it to be >0).

I already had pretty much that mindset but Mr Money Mustache accelerated it.

Congrats, awesome place!
Yeah absolutely - the idea is to not just buy the best and greatest of everything because you have the money. Same with cars - some people are car people and that's their passion and it makes them happy, makes sense to allocate a lot of money there and I'm definitely not putting that down.
On the other hand when I go to work and I'm driving a bottom 10% car while making top 10% money I'm thinking damn some of those people didn't think this thing through - they can't ALL be car people.
Then you have the safe rationalizations to not stray alone away from the pack (oh it's for the safety, my dad said you can't afford a used car, I need the SUV in case I go fishing every other year, etc.)

If you make more than 150 an hour then you don't have to worry about any of this nonsense, and if you make less than that and still have a luxury car I hope you're interested enough in it to wash it yourself.

Also, where is it that you hang out please? It sounds like good "happiness ROI"...

Ah yes, I was pretty much expecting Vegas

Yeah I mostly was kind of in line with both you and rotordave - if there's expensive stuff you own that requires a lot of maintenance money and that you don't care all that much about, there's probably better choices to be made, but if you either care enough about said thing to take care of it yourself or you make more per hour than maintenance cost, makes sense to outsource it.

That makes me think of another pretty famous book I read recently - "The 4 hour workweek". I think a lot of this is best case scenario, suitable to a small percentage of people, but there's a lot of it that makes you think about ways you could improve your efficiency.
Basically the book can be summed up as outsource as much stuff as you can, including revenue generation, to free up as much of your time as possible.

One of my good ROI activities this winter. 40$ worth of lumber, get good exercise, get some Vitamin D, entertain the kids.

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Mr Market! Did you read this book? I think it was the first book I read about stocks and it is indeed a good place to start. I think I remember they used the "Mr Market" idea in here.

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The peace of mind argument is perfectly valid, so long as you're conscious that you're putting a $ value to it.

One of the things I think most people pay too much for, and that I hadn't really thought about until reading Mr Money Mustache is insurance.

Insurance is basically:
[how likely it is something will happen to you] X [how much it costs when it does] X [1 + insurance company overhead] = your cost
Plus, the insurance company invests all that capital to make even more money.

So, it makes sense to get insurance for stuff that is unlikely to happen but will ruin you if it does, with a pretty high deductible that will not ruin you if you have to pay it, but it doesn't make sense to get insurance for something very likely to happen and that will not ruin you, because you are better off putting the money aside yourself and invest it and not pay the insurance overhead.
Unless you want to pay extra for the peace of mind, which you may or may not want to do.

Also to keep going on this riff, the old "you can't afford a used car" adage is basically insurance, peace of mind and not dealing with the hassle - you are sure to pay, say, 30k and not have to deal with the unexpected maintenance and breakdowns, but if you can afford a 30k car, you can certainly afford a 3k one with 1-2k of maintenance here and there.

Thinking about buying some property in Florida, and doing AirBNB with it with some local manager. I do have some relatives that could occasionally check on things or whatever.
The primary goal isn't FIRE, but I'd like the thing to pay for itself + some more to offset the trouble (I would want to use the property a few weeks each year too). Anybody have experience with this kind of thing?

FIRE related: I started cutting my own hair during the pandemic and I've gotten pretty good at it, no going back!

Cool, thanks for the feedback! I think I'll start by looking at what kind of mortgage I can get to see what my ballpark is... I figure property prices are going to keep climbing with inflation for a while so if I'm gonna do something, better sooner than later.

The property manager, how does that work? They charge you like a 15-20% and handle every single thing? Are you still the one managing the AirBnb account, but they take care of cleaning up, tending to whatever needs tending, etc.?

Ok, so definitely a big part of the equation, what service is provided by the property management and at what cost. As far as VRBO vs AirBnb, any particular reason?

Yeah really not interested in these 2 places in particular (and Daytona, Orlando, etc.) - my relatives are around Jacksonville so that area would be interesting although pretty expensive near the beach (Jax Beach, etc.). If not I'd like to find the sweet spot between very touristy and run down. I like places where you don't feel like you're in a mall all the time but you're not worried about getting stabbed either.
I also prefer the cypress trees and swamps to the beach but I'm not sure my girlfriend would agree and I don't think it's as AirBnb-friendly.

Noted!
Yeah the swamp comment was irrelevant, no way my girlfriend and kids would be up for that - just to try and outline the vibe I'd like ideally (like if there was a coastal Florida version of Austin or San Antonio I'd go for that, but I don't think there really is such a thing )

https://crimegrade.org/safest-places-in-miami-fl-metro/

I don't know how much this site can be trusted but it might help in seeing the more "stabby" areas.

Did some more digging into that - got in touch with a short term lease property manager whom I really liked and he gave me a few pointers. One of those is that he really doesn't like condos much - HOAs are a PITA and are pretty restrictive on BnB type stuff.
Another reason is that according to him, I'm better off finding a little family house further away from the beach than a condo closer, for the same budget, because you can typically charge more per night for the same investment and get better ROI.

For those that do AirBnb - what occupancy rate would you guess you have on average? Trying to crunch the numbers to see if it would potentially pay for itself or not.

Jacksonville area, not beachfront because I can't afford that, about 250-300k budget, picking the house mainly for its AirBnb-friendliness but someplace I can spend a month or 2 in the winter with my partner and the 2 kids. With an all-included property manager.
I figure if it's rented about 1/3 of the time it should pay for itself. Does that sound unrealistic?

Thank you Hench4Life and DanMarino - those are good ballpark figures, that helps me figure it out.
Yes, I'll also do my own research by trying to see availability from the renter's end on the areas / types of houses I'm thinking about.

Ever since I started looking on Realtor.com, I'm getting a bunch of e-mails everyday and I'm seeing many houses that seem ok to me for those purposes within my price range, but of course, location, location, location. They do typically look pretty expensive for the size but as long as the AirBnb market follows I guess that works.
I have a look at https://crimegrade.org/safest-places-in-jacksonville-fl-metro/ to try and only look at the green stuff.
Keep in mind that my primary goal is to spend only a few months (1-3) out of the year and for the rest of the time it should be AirBnB friendly, so I'm not looking for something that needs to be very large.

One thing I hadn't thought about until this weekend though is the HomeExchange thing - maybe that would be another way to get away from the Quebec winter and just have a change of scenery once in a while at little or no cost.
Still evaluating the scenarios - if the AirBnb could end up paying for itself I guess that should be my #1 plan.