I have personally been the guy who hasn't pulled permits and got caught...by far one of the worst experiences of my investing career.

I'm going to reiterate what's already been mentioned above, but I'm going to actually give you examples of why it's relevant to you to find a U.S. tax professional.1 - You're going to need to file U.S. taxes once you have property down here, there's federal filings, state filings, and sometimes local filings too2 - Tons of tax treaties between the U.S. and Canada that are easy to miss and can cost you a lot of money (important one with rentals - effectively connected income - if the professional you talk to doesn't know what this is, run away)3 - The amount of days you spend in the U.S. needs to be tracked and if you go over a threshold, all of your worldwide income could be taxable by the U.S.4 - Selling real property means up to 15% of your sales proceeds might not be available to you for years (FIRPTA)5 - Lots of nuance at the state and local levels, which both want to take as much money from you as possibleMain takeaway here is that you should find a U.S. based tax person.

Renting is the last thing I would do personally unless it is less than 12 months max. 

You have already admitted that you treat each person differently. 

Third, the typical person renting a room is not a home buyer candidate. 

Still can be very beneficial for a new investor but personally I think not as good as a service as they had with their exclusive listings where they had inspections already done, rent rolls available, and you can complete the entire offer/acceptance via their platform rather than being handed off to an agent. 

Hello all! :)Someone I reached out to on an off market deal told me that they couldn't sell because they bought the property as a rental in the 70s and didn't want to pay the capital gains. I'm curious if this has com...

If you're looking for a more landlord-friendly market, I personally recommend Columbus OH.

You have a freelance job and you can qualify as REP I sharing this from my personal experience.

I have two books to recommend, one podcast, and then one more summit happening in person in May for syndication investors.