It is a matter of how bottom-line-oriented they are and knowing how to file insurance claims.

The title company will handle clearing the title but won’t manage personal agreements.

In theory, you could QT the property to an LLC in your name and enter into a lease with you personally.

If Jorje works the same way North Carolina does, go to the register of deeds and learn how to look up substitute trustee filings.

If you aren't already aware what happens after the 1031 exchange, you may have to file tax returns every year for Oregon AND Portland every year after you sell.

You have to complete Schedule E if you have rentals.You should check if the turbo tax premier version allows the filing of Schedule E.With that said, using a software like Turbo Tax will assume you to understand what is deductible.If you work with a tax professional, you are more likely to have an accurate return.

Personal guarantees are EXTREMELY common.

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

We make people take photos of themselves holding their ID and then I also meet them in person for the showing - at least for my units on the NW side of Chicago.I've never heard of these testers, but I am not surprised. 

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.