I have had numerous issues with the PM not fixing things at all or in a timely fashion.

I'm having a hard time finding an explanation of the improvement requirements, and several sources don't even mention them.Are you sure the tax advantages are tied to improving the property?

Since then I've read, and continue to read, numerous real estate and self-development books. 

Maintenance requests are handled online as well, if a tenant submits a maintenance request, you recieve an email with the address, unit, tenant contact info, and their detailed explanation.

However, I can’t seem to find enough information (or at the very least a dumbed down explanation) of earnest money and escrow accounts.

Thank you for the explanation Luc!

@Scott Titus thanks for the explanation.

I could answer your long list of  questions here, but I would have to write a book...this isn't the format for a written explanation. 

He discussed the numerous pros to hiring a company in the beginning.

Your in over your head with that many properties, I have been to numerous Philly auctions and there is a sea of people who will just outbid you to the point it’s not even a deal. 30 properties is not feasible and chances are half of them won’t even be auctioned that day.