Like your post title suggests, you die to avoid the taxes.

Do they include energy tax benefits within their study?

STR-friendly markets make it easier to get started and grow your business, and the lack of state income tax is a huge perk.

However, it must not have been your or their intention to avoid tax. 

That said there are some nuances and requirements to property implement interest tracing so ensure you talk to your tax professional ahead of time and keep the funds movement as clean as possible. 

It will have to be a pass through/disregarded LLC to keep the tax payer the same and the 1031 valid.

If it's in a high tax /flood area taxes and insurance could easily be 5-6k or half that then with title insurance points and closing it could make senseWhat is the breakdown ?

They also have the Mortgage Tax Credit.

As far as flying (tax deductible too) You can do that and if it's in the states the total trip shouldn't cost you more than $2000 all in with lodging. 

There are, of course, also things like politics and tax policies preventing the New York side from developing its tourism sector to be on par with Ontario...