The area does not have explicit rules on STRs so its a gamble with that strategy.

Enemy method is great for establishing a baseline.

Since you're moving in soon, having face-to-face conversations can establish a personal connection and show your commitment to fair and clear communication. 

(Which these duplexes will be until an LLC is established) But I wonder if there are benefits to earning my real estate license? 

Its a gamble to go the permit route or not in Philly and absolutely matters the neighborhood/your neighbors as they are usually the folks that will call L&I on you OR if your property is near other construction sites where inspectors would be traveling to/from.

The trick is getting in front of the administrator, establishing rapport and getting them to a price that makes sense for everybody.

Thats not a wise gamble in most cases if there is a market change for any unknown range of factors.

Don't gamble. 

Give up a bit of projected return for an established operator.  

Ask discovery questions, genuinely care about the answers, and seek to find a solution that falls in line with what is important to the owner.Aim to first establish trust with the owner.