Not to mention, the boyfriend will not qualify as a tenant due to criminal record, insufficient proof income and several other requirements.

They don't appear to require any repairs.  

We found some we liked, and some that may require more work but I enjoy that aspect for what it's worth.

The alternative...if the lease specifies, is requiring him facilitate the sub-lease to a tenant approved by you.

@David Travieso first check state and local landlord tenant laws because you may be required to provide lodging or possibly just reimburse days not available, if damage was not caused by them.

Quote from @Elliot Mitchell: Anything worth doing requires effort and won't happen overnight.

But I also provide full management for a couple of others for 10-20% depending on minimum length of stay (since 30+ day stays require much less work for guest changeovers). 

In order to make sure you're optimizing your tax advantages and adhering to all applicable requirements, even while I can offer broad advise, I suggest speaking with a tax professional or accountant who is knowledgeable with real estate taxation.

As Stuart mentioned, STR in the Phila area, especially in Philly itself are not straight forward and require zoning and licensing requirements.

You didn't mention it directly above but I'm assuming you are planning on doing a 'live-in flip" in which case, yes, you should be able to get an FHA 203K loan (assuming you meet other FHA lending requirements).