The only thing that would be different is that Proper covers revenue loss + all the bells and whistles  I feel I don't need for 2x the cost - squatters/bed bugs.Any input on this from more experienced STR investors or others with insurance backgrounds please?

A property management company experienced with Section 8 is crucial.

That is the best and fastest way in and as long as you have experienced help, you will learn by doing far faster than aligning a career to help you learn.

With this approach, I can very easily vet borrowers (no newbies unless partnering with an experienced investor for example) and focus on those that meet my criteria.   

I'm more experienced as have been in multiple RE sales (with agents and directly with owners too) over my life and been an LTR owner for 15 years and just want to do STR at this point, but if this program is legit then I would be the one searching for houses while he did the calls.

With the appreciation you've experienced, have you thought about what's next?

We would typically not do this, but talking to a very experienced property manager friend, they agreed in fact suggested we let them out, this would be the one exception... crazy and aweful situation.3. 

Our strategy is to find properties in the Germantown, Logan and Olney areas of Philadelphia that need renovation, with the goal of holding and renting them out long-term.We’re currently looking to connect with experienced contractors who can help us accurately price out repairs and renovation costs for potential properties.

So its not at all like the Mentor/guru my client in Charleston experienced.. 

If you and your partner are excited to start a business, this would be the best time to discuss with an experienced attorney who can point out things you all never considered or discussed.