The pain point was that the seller grew up in the home.

Simple does NOT mean "easy" or pain free. 

Gettysburg, PA in (Nov, I think) 2021 changed rules for STRs.

I also am planning to meet with my PM on Monday to discuss pain points and better expectations, I would love to hear what sort of expectations you set with property managers?

I do have several S8 rentals, while they are generally performing well, there is more paperwork involved in the leasing and the strict inspections can be quite a pain. 

Servicing tasks can be outsourced to administrative assistance and new agents.If you have trouble with time management make this a daily habit.

LLC's have their place, but they are overhyped and new investors tend to overestimate their importance and underestimate the administrative effort.I have been a landlord for 15 years and well connected, yet I don't know anyone who was very saved by an LLC, so I asked BP nation:https://www.biggerpockets.com/forums/926/topics/1151922-than...

“Please, Learn from My Pain”)Leases: Month-to-Month MagicStrangers are like boxes of chocolates—you never know when one’s going to melt all over your sofa.

For larger buildings with financing, it's worth the administrative burden and the potential for higher churn, just for the sake of preserving occupancy. 

I missed a lot of flaws in that house and I had some painful years as a result.