it stinks because i live in Delaware and there is literally no multifamily units for sale.

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. 

Additionally:Is there a specific state where it makes more sense to establish the holding company (now that anonymity in states like WY or DE isn’t the focus)?

Big military base and probably lots of border trade if that continues.

This issue alone kills many HUD dealsYour agent must fill out the request form and deliver it to the FSM with the required $$$ to de-winterize. 

@John McKeeHi John, I can give a brief high level overview.A Delaware Statutory Trust (DST) is a passive investment vehicle that is generally used for real estate investing.

The metro area’s core six counties straddle the border between the states of Missouri (4 counties) and Kansas (2 counties).

@Jose'Luis De La TorreWelcome to BP!

In 1950 a law was passed that the City of Detroit could not expand its borders like other cities have done. 

At this point I'm trying to figure if I should try to bring in an experienced partner to de-risk this build out or scrap the plan altogether and sell.