Regardless, it speaks to him being a high maintenance person I don't want to rent to.

Nowadays I use what I've learned and help investors building their rental portfolios in class C neighborhood while personally I either build Padsplit in class C or build high end vacation rental in class A area and hold them. 

I haven't personally gone myself, but plan to soon.

Usually contractors in Philadelphia will carry commercial general liability coverage which covers property damage, bodily injury & personal injury.

Recommend only one person notifies him and not two.  

I tried self managing my first year, it didn't work out great as I rushed and rented to the first person I found.

A queen bed is 5'x6.5' which wouldn't leave much room for a person to walk on either side, a night stand or a dresser.

Personally, with one of the rates that I have on a different duplex - I would consider doing a refi if rates dropped 2 points because I know I'd be cashflow positive and could hit the LTV with updates that I've done to it over the past 6 months 

As a side note, all my tenants have my personal number.

You can look up the owner at your county's site.Join your Local RE club and attend meeting in person to meet people and learn.