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

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. 

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.

There are guidelines and guardrails, but a challenging deal can have positives and a golden deal can have issues below the surface.

So far, it’s going really well, and I’m glad we made the shift.For me, the decision wasn’t about issues with self-managing but more about freeing up time and mental space to focus on the next steps in our investing journey.Curious to hear others’ experiences as well!

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. 

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

We agreed to address the issues left by the previous tenant and you did not want us to handle it.

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

This is a trust issue.