I'm looking for a short-term rental (to generate active losses), but maybe I'm thinking about this wrong...  

How would you suggest I use this money to generate the maximum amount of monthly cashflow? 

Collecting ID and CC pic has eliminated UNTIL now we realized some scammers had used AI to generate the CC info onto a generic CC pic and also used AI to generate an ID.  

My investment goals are modest (say, 9-10% IRR over a 7 yr period) and I am convinced Philly will not generate that.

You'll need a lawyer to generate the paperwork and filings and experienced enough to give you general advice on the process, help you establish appropriate compliance and back office procedures.

It crosses generations.

This means that for every $1 of rental income you generate, you save $0.35 in federal income tax.You mentioned an Illinois state income tax rate of 7.75%.

Seems like most people use wholesaling a starting point or a way to generate capital.

I know others will likely beat me up over the way I do things, but for me if you have experience buying and rehabbing properties then I would do that to generate the money you need to do bigger deals. 

A marketing company who does direct mail or something to generate seller leads?