Install central air and the next thing this guy is likely to complain about is his high electric bill.Keep in mind that in many states a landlord must provide reliable and working plumbing, electrical and heat. 

Consulting with an attorney specializing in Pennsylvania tax liens could also provide you with more tailored advice and help with negotiations.

Do you have reliable and affordable insurance?

I would definitely consult/call the property tax assessor's office in whichever county you plan to reside in to be 100% certain as they will be able to tell you. 

As for getting a mortgage, you will need reliable income and some W2 to show the bank.

You should be consulting with your CPA ot tax preparer to account for the specifics of your individual tax situation. 

Hi,Regarding your questions:#1) I highly recommend you consult with a licensed insurance professional in your area, especially one experienced with landlord-specific insurance.

This was in VT, I would reccomend consulting an attorney in MA.

For lenders/banks, quality vacation rentals are clearly a unique and reliably performing asset class..For investment properties these lenders typically require a minimum 20-25% down payment but since there is higher gross revenue, the investor can often qualify for a higher loan amount.

Is there any reference I can consult for guidance on these issues?