@Cody M.I would add a Phase I Environmental Site Assessment as a contingency to any offers on properties more susceptible to environmental issues (dry cleaners, gas stations, auto repair garages, etc.)

Transparency always wins.3)Make sure to have mattress and pillow protectors, top-notch cleaners that take pictures of every sheet as they lay it before guests get there, and consistent pest control.

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.

Our cleaner says she has another house on the lake that does Fri-Fri and fills the whole summer...unfortunately (or fortunately) there aren't a lot of other STR large lake houses around for us to comp.   

They have a team of cleaners. 

Please don't message through Airbnb as owners find it annoying as they get hit up by cleaners, instagramers and property management companies all the time this way and many of us mark it as spam which could kill your Airbnb account. 

Could you merge LLC-B and LLC-A before the sales process and do a cleaner exchange? 

I'm paying above average cleaning in the Colorado mountains because our cleaner is trustworthy.

My cleaner's always clean on checkout day.I don't want trash sitting there as my cleaner's take the trash.

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.