Mainly because I am a rookie, but also because I did not know these questions to ask when starting out. 

. $219k - now $500k market price in very southern Maine/NH border.

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I know one of the main qualifiers is it has to be owner occupied - which is fine.Will there be any issues with this second purchase being in the same town as my first MF home?

you will have to put some time in. also, not your main question, but: wholesaling is spectacularly difficult. 

Hey Zach my main goal is to find a partner to work with.

Many are using Orlando and the surrounding area as an example of why STRs are no longer viable.Most of us know that the greater Orlando area is super saturated and that the main money makers are the huge places that sleep 20+ with incredible themeing in just about every room.There are plenty of areas in the USA that can support great returns but like any real estate purchase, you need to do your due diligence.

Driven by favorable interest rates and stock market performance, debt issuance has been the main capital driver.

I live in Maine where short term summer rentals are in huge demand.

The PO Box mainly won't get used but in future I plan to use the address with any tenents.