Once you have them in there you can have a cleaner come in and tidy up the shared spaces weekly so it stays nice. 

If so, such are better sold than leased, either way you'll be using UCC filings to secure these assets.I'd suggest you simply sell with seller financing and use a deed of trust/mortgage, it would be much cleaner and much easier to manage.

How do the hands-off people not deal with receipts from contractors,  handy people, cleaners, etc I don't know.

Have you looked into companies that specialize in this like Stericlean or Crime Cleaners?

I've seen so many situations where a billboard company took an unsuspecting owner to the cleaners and signed a perpetual freeway billboard lease for less than $1000 per year with no increases.

Relying on roofing contractors to do it is a good way to get taken to the cleaners. 

I will say Attom has upped its game in the last few years concerning ML and AI.... so who knows, they might actually have cleaner data now, and overall it might be cheaper to buy from them as a reseller.First American are quality people, and they are scrappy... they have a huuuge database of scanned doc images that they have run ML against for the juicy tidbits of data a county/city does not collect or load onto public-facing .gov sites.Most of the data you are looking for, like accurate monthly parcel/assessor/people ect data can be had just by googling your county name with 'open data GIS' in the search string.

Everyone from your Agent, Cleaners etc should be people you have vetted prior to hiring.

For 'special' tenants who are not clean, you may want to line up cleaners to come in the day after they move out and advertize it for rent starting on the 15th of the month. 

However, we have a team of cleaners, handymen, plumbers, etc who handle most of the issues, which allow us to be remote.