If you control how they perform tasks, set their hours, or provide tools, they should likely be a W-2 employee, requiring you to withhold taxes and comply with payroll regulations.

However, a lot of concerns can be mitigated with looking at their past rental behavior in a lot of different settings.

Unfortunately, I do have a property in an HOA, which often comes with their own set of rules that you'd have to follow of course. 

You can have an email for each account and you should be able to set your phone up see multiple accounts at once should you get inquiries or messages.Just log into each account to make updates and price changes.

Let me know if you need any tips on working with contractors or setting expectations.

LLC offers better legal protection.3) Setting up in states that allow your identity to be hid is also overblown.

Also being able to write down/document goals I set earlier and see if they are being hit.

They're basically two different skill sets and it's fallacious thinking to assume you can do one because you can do the other.

Set it up once, and let it do it's thing in real time. 

Setting up the listing really wasn't that difficult.