My dilemma is that my mortgage payment is $3100 and the max rent I've seen in my area is $2800 so I wouldn't be able to rent it out. 

No one likes putting in their info for help and getting 30 phone calls in 15 minutes! 

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.

You don't have enough money for the deposit so how  do you plan to obtain the necessary funds to cover the closing costs? 

However, this would be putting 2 attached units in front and 2 attached units at the back so don't think that would fly but if it does that would be fantastic.

And my agent for the replacement was already my property manager for my other rentals so I used their realtor service.

A "wrap" involves a a sale, so if you don't want to sell, you don't want a "wrap".

Alot of details go into pricing out income and expenses so using the BiggerPockets Airbnb Calculator could help see what expected expenses you can expect. 

I asked the architect to stamp the plans so we can get the permit and he responded that he can't stamp the plans, and they shouldn't need them because we can submit the stamped site plan from the surveyor and his drawing together.

The biggest challenge I have right now is choosing a company to set up the homes they are all so expensive.