We have friends from Chicago and while you can make some serious money there - they retired based off of many years of good rentals - you have a lot of tenant-favored laws and attitudes to deal with.

You might be the same...if you don't like roommates now, I doubt a househack is in your favor.

There are intuitive reasons why suburbs have steadily grown, and as technology increasingly enables us to over come the logistical effects of distance (the COVID-19 social experiment will noticeably extend this ability) we also become less concerned about the logistics of distance in favor of quality-of-life for our families.Appreciation is where the most money is made, and the fast-growth areas are where the most appreciation occurs (for 10+ years).

The downside for the seller is an owner occupant can’t buy it, at least not with the favorable terms as they won’t be able to make it their primary within 1,3, or 6 months depending on lender.

The limiting factor of being able to invest in real estate is always, always, always how much money you can access under favorable terms.

so if it falls in my favor i will definitely be buying title insurance! 

We managed it long distance from New Orleans starting in 2010 and sold it when the market was more favorable for sellers.

And to one of the options you mentioned, you have the ability to leverage yourself in a very favorable position w/ low money out of pocket and have a portion of mortgage paid by a tenant(s) while your home continues to appreciate.

And I expected terms to be less-than-favorable the first time around.Did you actually apply for a loan from anyone or you just made a few preliminary phone calls?

I'd like to think that $45000 in gain can count count as long term capital gain and be subject to the more favorable rate.