Should I re evaluate what strategy I should use and maybe look further out in places such as Rochester and BRRR properties out thereHey @Jared Leggett, I know I'm jumping in here late in the game, and I have to admit that I haven't read all the many comments you've gotten, but I wanted to provide what I imagine and glean is a contrary view.It is easy to dunk on NYC for young investors starting out, but if you are a first time homebuyer you can buy a $1M property with $35k down (+ closing costs which can be avoided with seller's concessions).

To me it’s a challenging game, an intricate puzzle where if you learn how to play you get great results.

Just suck it up in the short term and reap the benefits in the future.

He appreciated my passion and wanted to help me get to where he is in short time.

He is the best and sells nothing.Your idea makes sense, but as you've seen with regulations, it won't work in practice for a short-term rental.I like @Dan H.'

Buy close to Notre Dame and the nicer areas for game days, graduations, and families visiting. 

or Do I turn the Fl house into a short term rental property and look to finance the 6 cabins?

There's some connection you have to this person with money who is looking to invest it short term and collect an x% return. 

Bob arranges the money for Joe, so the bank is short again even though Bob could have paid more on the debt.

I don't think my manager does that for the short term side either.