If you sell directly to a homeowner, the issue can come back on you and bite you in the a...  

So far, I haven't had any issues renting my unit.

We currently use Hospitable for 12 properties, and it's working fine, no major issues, and I know they've been expanding with new features.

Are we technically serving alcohol? 

@Kyler Tarr it's good you haven't had an issue but you also mentioned your property has some knob & tube.  

Our main issue is these properties are owned in an LLC.

Just curious, is there any tax benefit to filing as a regular partnership and issuing k-1s to ourselves that show a loss?

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

We have had a pipe burst during the cold winter months, the roof needed to be replaced (thankfully covered by our insurance), and some issues with electrical, which hasn't been majorly updated since it was built in 1973. 

If the drywall cracks in the next year or two, or the doors start to stick, then you likely have a larger settlement issue going on, and will likely need to call a foundation repair contractor.