I have solid team in place for now but I am dreading having to find other reliable cleaners as we expand. 

I now have a $0 transaction which looks odd.Option 2) Keep the original expense for the previous year, but add the refund for this year as income.This sounds cleaner, but I’m not sure how the refund should be categorized.

However I don't want to get taken to the cleaners for hundreds or thousands for someone to essentially say "yep, looks good."

They are not easy by all means but with only a few systems set in place (STR specific cleaner, auto messaging, keyless entry), they are not that much work to self manage.  

Do the owners do the laundry and put towels etc in a closet for the cleaners to put out?

For this reason, I'm thinking about charging an extra cleaning fee if leases are renewed or offering the guest to have a cleaner come in at their expense (if it were me and I had to pay it either way I'd pay the cleaner and not have to do the work myself).

You need to spend time finding a good cleaner and handy people to take care of things.

. - Does opening LLC or Trust and transferring property to that make it a cleaner transaction?

Then from there you should reach out to them, see if they have investor friendly agent, and if you find a good agent, you should be able to get connected to cleaners, maintenance folks, contractors, and more. 

ie finding cleaners, setting up messaging, getting 5 star reviews, staying booked, finding the right property…Comment what you thought has been the hardest part in the start of the process!