—used algorithms and insider information to keep rents artificially high.

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.

Pensacola has a lot of potential, and I’ve seen investors do really well in the area with both long-term and short-term rentals.Since you’re just getting started, here are a few tips that might help:Know Your Market: Pensacola’s mix of military families, college students, and tourists means there’s a steady demand for rentals.

.: Stessa isn't good for keeping track of tax deduction items.Stessa was designed to just look at P&L.

We routinely turn off boilers during the summer to prevent them from running to keep up to temp all the time during the warm months.

Appreciation, in particular, is crucial, while cash flow acts as the fuel to keep the property sustainable.Your Scenario with 2% Home AppreciationHere’s how the deal looks using your assumptions:Year 1 Analysis Cash Flow: -$1,123 Initial Equity: $51,000 (assuming a $249k purchase on a $300k market value as per your report).

To defer all of your gain, you'll want to trade up in value, replace all the debt (meaning new properties have at least $350,700 of debt), and not take any cash from the exchange (this is boot which = taxable gain).As for replacement property, it just has to be real property - meaning it can be commercial, STR, land, etc!

Zillow has a lot of valuable information, but keep in mind that it's algorythms don't work in every market. 

If you’re not occupying the property and plan to either sell it or keep it as a rental, you might want to consider a bridge loan through a hard money lender.

Being out of state, I would suggest vetting your "team", meaning find an investor realtor, lender/s (hard $ / long term), property manager, contractors, etc.