The two options I am looking into are House Hacking and Wholesaling. 

Two months ago a guy showed up at my office with a truck full of family and a large trailer full of belongings.

The two things that came to mind when I saw this were seasoning (as previously mentioned) and potentially property value? 

@Grant Francke Here is what we recommend to our clients:For Landlords- Have two bank accounts one for receiving rent that is received from Buildium and another bank account for everything that is not received or paid via Buildium.- As Buildium has all the details of the tenant, there is no use duplicating it in QuickBooks.

In Florida where I live, those two items cost me about 25-33% of my monthly income on a LTR.  

Particularly in Philadelphia where there’s a ton of red tape to navigate and construction costs are disproportionately high relative to other markets.Ten years ago I could walk into a district L&I office, complete a two page application and pick up a building permit without plans for a single family renovation the next day.

At this point, this tenant sounds like they're all bark with very little bite - I'd just keep documenting everything in writing (as it sounds like you've been doing) and sending everything to them via email as a backup as well, and only involve the lawyers if the need actually arises (e.g. if they file a rent escrow action; if you need to start eviction process for non-/partial payment; if you get them to agree to a mutual lease termination; etc).If you do end up going with the carpet replacement option, I would also recommend going one step further: in addition to replacing the carpet and the padding underneath, also take that opportunity to put down a coat or two of heavy duty Killz on the subfloor before the new carpet gets installed. 

Yes, I did two live in flips when I got started. 

~That's just my two cents!

@Blake West I was just in Waco two weeks ago and ran across a great contractor or two during my scouting trip!