We have a pretty solid lease that has served us well on our properties but on the most recent move-out by a long-term tenant that always paid early, we had to clean from floor to ceiling and everything in between. 

Because of this, they have changed their fee structure on me two times in the past two years2) They don't have back up cleaners so when the cleaner can't clean, they block off my calendar3) They do not have easily legible financial statements and do not provide 1099s 4) They have made decisions that have required my money without consent5) They block off check-ins on Sundays6) They are not great with technology - though they try to use hostfully to list on many platforms, I will frequently see that my listing is not up on VRBO for example.

I have properties in the city that I allow pets bc I know those tenants will be required to clean up after them per city laws.

Steam cleaned the carpets, etc, and he determined there was no damage.

I'm not sure how well versed they are in the trust details but it makes sense that it would be due to the step up basis so if there's a way I can approach them to give them a solution to that, that would be great. 

I would call professional paralegal solutions.

I feel it's a bit unfair and frankly I am not going to charge the tenant anymore than what the place is worth market rate because of its location and he is a great tenant (pays on time, keeps the place clean, communicative etc) I feel like i should even give him a break because he said he couldn't even be home since there was construction all summer due to building maintenance repairs. 

Find out what a typical nightly rate is for your area (not what air bnb charges, the actual nightly rate the owner will receive not including the cleaning fee).

We rent single family homes, so we have a conversation about yard maintenance, snow removal etc - have you don't this before, do you have the tools etcI also bring up house cleaning questions, by telling them we had a tenant who did not own a vacuum cleaner, did not know how to run a dishwasher, had a mess in the basement etc - and then see how they respond.That is a non-offensive way to talk about house cleaning and you'd be surprised how different the responses are.

But they’ve asked to come up with a solution since the loan isn’t technically assumable - something equivalent to acquiring the LLC that holds the property.