You're basically asking the HOA to rewrite the CC&R's on your behalf, and that's not going to happen.

I will need access to some online system to send/receive offers and counteroffers electronically? 

You definitely don't want a commission split nor do you need the systems and training that the larger brokerages offer.As far as your own purchases, you could start out using a lawyer to review documents and help you understand everything until you have a better grasp on it.

I am fairly familiar with small claim system as both a tenant and a landlord. 

So school system does not matter, commute doesn't matter.Our oldest is 2 years old. 

If the house has been vandalized and copper stolen, you are also looking at an extensive amount of sheetrock damage, usually doors, possibly broken windows, damaged plumbing fixtures, and damaged HVAC systems.

Using the BRRRR system, once I refinance the home w/ the equity i’ve added, does the mortgage now reset to the new value of the home?

Not sure yet what I'd do if I buy 123 First Street and 123 Second Street since my system wouldn't allow me to use "123" twice.

Nothing against Philly but do you have any systems in place to manage at a distance? 

I would just go so far as to put a system in place to enforce and make sure that all of your tenants have renters insurance.