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. 

Is there a reason that you need such a complicated structure?

The loans were varied and some were able to close sooner than others and they wanted to close before the others but we held out because we needed to close all of them at the same time to avoid any last minute standoffs or complications.

So this might also complicate matters significantly as I would probably need to add both an additional well and an additional septic in order to truly split these into two separate properties. 

Without a permit, the rental income might not need to be reported, but this approach risks legal issues, loss of tax benefits, and complications during audits or resale.

Complicating things is I like the property and have an itch to purchase.

this is a specific need you have and maybe there are attorneys here on BP in NY that can help, but having worked with jurisdictions before - with it being early december - these officials do not move very quickly so hopes of closing before year end could be complicated.

Or was it too complicated or frustrating to complete a search that way? 

Real estate's low liquidity can complicate required minimum distributions (RMDs).

Hi Guys...1st post, although I've been following BP now for a year. I appreciate the willingness of the group to share knowledge and am learning a lot via the postings and videos.  Thank you, first off.I own and live ...