I have done extensive research in the risks, how to structure such deals to mitigate those risks as effectively as possible, and legal considerations of each strategy. 

You also will still need to manage your property manager  - ie, stay on top of expenses, ensuring your property is being managed effectively etc. 

I’d love advice on leveraging my existing assets, navigating seller finance deals, or other tips for scaling effectively.

Unfortunately, this problem waste a lot of my time that could be spent on other investments.I have used the same tax professional for many years and he is very educated, but also much older than me and it's hard for me to understand all the reasons he has expressed why is better to put the rental on my personal tax returns.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

That is essentially a waste of money.

To newer investors, they may rely on their agents to act as the Chief Investment Officer, effectively thinking the agent will bring them only perfect deals that meet their investment objectives.  

This was a cost-effective way to meet our requirement of providing just a stove and refrigerator (we don’t include washers or dryers), without breaking the bank further.But here’s the twist: If we were upgrading appliances for a long-term tenant with a stellar payment history, we might invest in brand-new appliances.

Plus each house sitting empty for t months seems wasteful.)But it’s hard to find a warm but not hot and humid location.

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.