While flipping is always a great play, Philly has an emerging rental market with an average $1000/month rent cash flow.

I've learned that playing SLOWLY is totally fine.

Both of these factors plays a role in my thinking hey maybe they would be to sell if I found a lender that can close fast and pay cash.

I've keyed my excel spreadsheet to correlate with tax line/form reporting so preparing taxes at year end is an absolute breeze (plug and play).

They don’t have washer and dryers (or hookups), our property does, we also have a small front area with grass the tenants can let their kids play in, etc.

I feel like this may play a factor in how willing the county is to just get the property "off their books."

I don't back on appreciation plays, but would never buy where I know there won't be any appreciation, unless that cash flow was just amazing.

I suspect there IS a tax play to be made with mal-investments, but I think there are multiple reasons it happens. 

Furthermore, I currently own a rental property that in the case things start becoming bad in the near future and I have to sell it, I would have more buffer to play on pricing as I would not need to pay commissions to a selling broker. 

Won't play by the rules of common decency you say?