What do I need to do to cover myself, and is there any advice out there for how to handle this in an ideal manner?

Ideally it would start as an Excel spreadsheet and then move to a reporting tool like Power BI.

Not to mention, ideally, you'd like a condo with reserves - no way to collect that unless the monthly fee is higher.

I have considered looking into other areas in my state that aren’t as competitive, but have also been intrigued by an out-of-state rental.My question: what experience/thoughts do others have about purchasing a property in a vacation area that will serve as an occasional vacation home for my family and myself and but will primarily serve as a rental - not sure if there is a term for it, but minimum one-week rentals and ideally snowbirds who will rent for a month-6 weeks or so during the high season.In my very preliminary research I have seen there may be some additional tax considerations but I’m wondering if this ever makes sense?

Ideally I would like to spend under 500 per month for rent. 

@Remington Lyman, can you e-mail me your list?

@Lynnette E. - thanks!

I know I'm asking for a unicorn here, so if y'all have any other ideas about what I can do to get the ball rolling (ideally not house-hacking) I would greatly appreciate it. 

I personally would rather go with a local lender, sacrifice .25% interest rate but ensure my closing happens on time and doesn't complicate the purchasing process then that is ideal.

It’s prime for people who use the highway daily for their commute which in Philly could include Jersey or Delaware, quick access to a highway and/or bridge is ideal.