So I'm doing the preliminary work in the meantime--contacting the city to see what they would like, reaching out to the residents in the neighborhood, etc That's great that you are doing your research beforehand. 

Owensboro, the state's 4th largest city, has a population under 100K, and many OOS investors prefer cities with at least 300K residents and strong job growth.

Investment Info:Single-family residence fix & flip investment.

So you may not NEED a lease signed for your primary residence already, especially since that's a lot of stress to find a new tenant and have a lease in place while you're under contract on another home.

If so, I would definitely consider a shorter-term lease or MTM lease to get you into that period and re-negotiate with the current resident or re-lease it at a higher rate. 

Cross border taxation is very complicated, most developed countries like the US and Canada have sophisticated systems to ensure their residents pay taxes, and you are not likely to be able to achieve your goal of not paying Canadian taxes on Florida income while a Canadian resident. 

The guest rules state no partying and it is abundantly clear our houses are in neighborhoods with full time residents they will be caught and they will be removed without refund. 

And once you convert it into your primary residence it is no longer eligible for a 1031 exchange. 

One parent can stay home through college. 

Plus, it puts your personal residence cost into the financial mix.