I have left my previous rentals cleaner than as found.

That is very low and hard to imagine.Self managing remotely is easy if you have a good cleaner and handy person on standby.

They must look at properties like you do.2) Meet with contractors, handymen, and cleaners in person and make sure they understand your situation and what you expect.

Also, persuading professional cleaners to log time may pose an issue. 

Separate LLCs with their own bank accounts tend to keep things cleaner come tax time. 

For cleaners, also check vacation rental hosts Facebook groups.

Totally a viable option but keep in mind the documentation of the process and making sure that YOUR material participation does not exceed anyone else in the home - for example, your cleaners or maintenance people. 

Most cleaners are not going to comply with your PMS platform protocol for cleaning and 98% of the functionality that you are going to use a PMS for will be messaging.

Obviously, we would hopefully hire a trusted cleaner, but any other advice on managing a property from a distance?

You can create sub-accounts for each property and create virtual credit cards you can assign for use with certain properties or with certain providers like your cleaners or handyman.