Any tips on balancing renovation costs with tenant expectations when preparing a property for midterm stays?

We want to get a Vacation Rental Permit for stays under 30 days for ADU but current zoning doesn't allow it.

Stay away from these guys.

Airbnb with a minimum of 1 month stay could be a good reference too. 

One of the greatest, most important lessons has been, staying in my lane!

Over the next couple of years, I don’t plan to use the property often, but I may stay there occasionally when it’s not occupied.

You GOTTA use WIDE-angel photos. many phones have great features for this now, or there is app's for it, or lenses, lens adapters. get something, anything, or buy a new phone that does it.

You are correct; it would be awkward having two different parties staying on the property. 

Stay in and be part of this 721 or lose my investment most likely.

I just stayed in a hotel in Moab and we had an A/C issue and it took two days to resolve and, honestly, that's not that out of line with my normal experience at hotels.I don't know where people dreamed up this idea that all hotels have someone waiting outside your room ready to resolve anything in 5 minutes.