I wish I had been able to make this!

I think you’re absolutely approaching this the right way—creating a job to retire to, rather than just running away from your current one. For sure, financial freedom—and the economic upside of real estate—are major reasons I’m getting into real estate. It’s a way to supplement/fund our household income in the future and, for now, offset my wife’s earnings. Those are the primary drivers. But at the same time, I’m drawn to rent-by-the-room and self-management because, if I’m honest, I like work that’s task-based. I enjoy picking up a concrete problem, solving it well and cost-effectively, and moving on—much more than slogging through endless, workplace work. Right now I have a government job where I work from home 100% of the time, and it isn’t challenging. I used to think having nothing to do would be ideal—no stress, no worries, just all the time in the world to read and learn languages, etc etc. In reality, if you’re an active person, your mind fixates on small minutiae in the absence of important things to do, and that’s not healthy. I’ve read this happens to a lot of retirees too, which is why I think what you’re building—something engaging to do—is great. Given that you earn a good salary, the real question is how much longer you can tolerate it. That depends on your financial position. If you had something like $5 million in assets, why wait? With $2 million, you might already be fine; $3 million is amazing and really depends on your expenses and risk tolerance. In your case this is very much a HENRY / ChubbyFIRE question. Could you “coast” for a while—do the minimum for a year? Or maybe your personality won't allow you to do it. If so, you might aggressively pay down mortgages, like someone mentioned above. The other option is to find a different, less stressful role while you continue building your real-estate portfolio, depending on your numbers.

@Jarrod Ochsenbein I think my number one concern would be zoning coming through and declaring 8 bedroom houses illegal in a few years. Which is actually the reason I'm interested in 3-4plexes in Chicago, because I want to turn living rooms into another bedroom -- so I can get 9-12 people under one roof (since the buildings are already zoned as 3-4 units. My second concern are tenant and roommate issues if I go for a lower price point, I suppose.

@Jarrod Ochsenbein yes, I’ve learned a lot from listening to @James Dugan on the calls! Didn’t realize he was doing multiplexes, I’ll have to ask him more!

I hope to make the next meeting. Would love to talk with everyone doing this model.