I get the general gist of it but also know it’s a little more complicated than the videos make it out to be.

(In the simple / non complicated scenario)- time ranges - in the best / simple case scenario how long should I expect this process to take? 

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.

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.

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. 

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

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

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.