I really would love something that can help us establish what we made from x property, what we need to pay for the debt service and expenses for the month, and automatically distributes the positive cashflow into our accounts or something of that nature to make things more automated and organized.Does anyone use something like this?

The presence of any of these conditions does not automatically mean you can not get coverage but depending on what it is, your cost may increase. 

And making sure that each time they stay in it they have some projects they can work on (painting a room or fixing the automatic sprinkler system etc).

This may not be automatic though. 

With most utility providers you can sign a landlord agreement where when a tenant leaves and requests a shut off, it's automatically switched back into your name.

Since leases automatically renew upon their expiration unless otherwise disclosed, I want to make sure I'm doing this correctly.Any advice is greatly appreciated.

I find the "space travellers" are unfamiliar with the area, and they are starting off upset (edit note:  spell checker must have changed the spelling I used from "Pis***" to "upset") because they had to travel so far from home base...and mentally that already sets their calculater up automatically multiplying every number by 90%.2 - "Be prepared with comps that favor what I need the numbers to be for after I got a low appraisal". 

Plus once the payment has been processed, it's automatically tacked in the system against the corresponding property.

@Michael Baum thankfully VRBO and Airbnb automatically updated the tax amounts in January.

Nor, does it give you the option to apply your credit score and automatically update the rate.