Unless you're able to save to double your downpayment to $100k plus it might make sense just to engage in these markets you outlined and see what's available that fits your criteria.

I would first check the zoning laws

As soon as I create the LLC, I go to the bank and open a checking account, savings account and apply for a credit card in the name of the LLC.

People decided to enjoy your space before they ever opened the door, and they'll forgive a few small things and leave a 5 star review when we feed that enjoyment every step of the way - from reservation to arrival to check out. 

Check out Onyx Insurance Brokers.

I would also make sure you perform a full background check on both of them prior to approving them.

https://www.biggerpockets.com/...Don’t know where you are in PA, but check out this string for my feedback specifically about PGH

For Medium term rentals, check out Furnishedfinder.com as a good place to get estimates for what you could rent your place for on a medium term basis.  

I haven't heard of camelcamelcamel but am definitely going to check it out.I just wanted to mention that Turno can be a good source to get an idea of what to pay your cleaners, even if you're using someone you've found elsewhere.

Check out Evolve.