@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.

@Christopher HoltYou'll want to become an MAI and if you already have your basic classes completed so you can start as a trainee that may impress your new boss.  

😎I've never required my SF buyers to get lender's insurance in my dozen or so sales, but I made sure to use a REC, not a Note and DofT. 

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.

Many people skip the whole LLC and just get an umbrella liability policy for themselves to protect their assets which is what the LLC is basically there to do.

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). 

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