If they have a 2 or 3 month period for a down season and it is hard to get a short term renter how easy is it to turn your place into a corporate rental for a few months. 

But not included in the $20k per month is the appreciation value during that period also the leverage at point A.  

I'd love to hear your opinions on good ways to find tenants that are reliable in the 30 plus day rental time period. 

It took a period of time but it finally got resolved.  

Most need to be repaid back, but there are better ones out there that do not need to be paid back as long as you live in the home for a certain period of time.There is a nationwide grant available that we use called the WISH grant. 

One being to have a balloon payment but amortize the loan over a longer period.

Make sure that you have an inspection period of a couple of weeks to get contractors, inspectors for roof, foundations, electrical, plumbing, etc to make sure it is not needing too many repairs.From what you have said, it sounds pretty good.

Once they take off property management, they tend to find it's much easier, they are occupied for a longer period of time AND they save 8-12%. 

I have checked periodically over the years and even called VRBO (they were no help).  

Philly is a small city so C class areas could be right next to B/A areas.You could also try and target MLS properties that have sat for long periods of time and try to submit a lower offer.