If you can answer these types of questions you will know what is important as you game plan for the next 10 years.

Ask the township for their 3-5 year development plan...

Projected sale: 950-990k Replacement property budget: 990k - 1.1M Plan: rent out the replacement home until meeting the requirements, then move into it while renting out a portion of the home via short-term rental 

Good luck.I also plan on visiting PR(san juan for now,  maybe ponce as well) in November for fun and to learn more.

I would also weigh if you plan on staying in the home you are in now for a long time or move in the next 5 years.

I'm going off the understanding that you still need to spend 500+ hours in the business to achieve material participation (please correct me if I'm wrong). 

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.

This is who will approve or deny your plans when you apply for a permit.

Trust.I am spending upwards of $7K having my STR to LTR back to STR repainted and refurnished.  

Don't spend time looking for something that doesn't exist.