Is it worth it to take on the extra work, existing or potentially new local ordinances, and seemingly new daily competition for a higher return or have I already missed the boat?

To me is seems like 3bed/2bath is a nice sweet spot for some areas of Pittsburgh where people are looking for an extra bedroom/office for work-from-home.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it.We have a 12 page management contract that we've added our real experiences to over the years, with the intent of protecting both us AND the landlord.

This passage followed a discussion of the benefit of paying extra mortgage payments towards principle, so I can't imagine what else the advice would have meant.

They even left the laundry room open to the public for some extra cash.

It may sound nice to pay a 5% management fee but the extra fees can add up to be more than the other company that charges 10% with no add-on fees.

Would I be better off leaving my current home alone (to pay it off sooner) and investing in 1 rental property with my $40-$50k or would it make more sense to pursue a cash out refi, convert back to 30 year mortgage, and see if I can purchase 1 or even 2 investment properties with the extra money? 

In some case our painter has had to do 2-3 coats in order to get the color and texture right on a flip house, which in turn will cost extra.

They could even gift extra money to you, so you control and manage it. 

It may sound nice to pay a 5% management fee but the extra fees can add up to be more than the other company that charges 10% with no add-on fees.