It’s great to hear you’re ready to take things to the next level in the residential space.

There are no municipal-level rental restrictions. 

Once you know who in your circle has $ to invest, you then need to understand their risk to reward level so you know what deals fit their bucket.

I think some min level of regulation benefits everyone, including wholesalers who currently operate in no man's land. 

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.

Is it single level?

Generally they are not rolled into the loan, and it's more the level of fees (say the percentage) they charge rather than any "junk" fees or costs.

What's your experience level at this time? 

The greatest control point is before that first lease.

Centralize your back office / use remote employees / VA where appropriate to cut costs and improve service levels / responsiveness.  5.