Time to go to Facebook, Craigslist or TurnoverBNB to see what cleaners are working the area.A great cleaner can handle some of the things you have listed for your assistant. 

If there is a different forum that is a better fit for this post, please let me know.The driveway is steep and gravel, and our handyman/cleaner (who worked for the previous owner and knows the house and its history well) suggested we have concrete poured to help with guests spinning out / getting stuck.

Having to set up PM, cleaners, handyman, etc. 

My cleaners are through turnoverbnb.

Totally worth it.Just get yourself a solid handyperson and cleaner.

Our cleaner came as a referral from a contractor that did some work for us when we bought. 

Our cleaners charge $175 per cleaning - this includes linen service so they can flip the place pretty quickly without needing to do much laundry.

It would seem they triggered an obligation and used up lifetime exemption with the large cash transfer.With professional advice, this could have been a lot cleaner... 

I really don't know, but just read stuff here and there on BP.However, I think the aforementioned idea of having limited partners / non-managing members is much cleaner. 

If you have a good handyman, painter, HVAC person, and cleaner, please let me know.