I 100% think you can find almost all these answers for free though through different channels online, BP Forums, studying others, and just trial by fire.

I started a 14 day free trial with Deal machine. 2 days I've found 80 properties I want to go after.

My best advice would be some kind of 30-60 day trial period to make sure the 2 of you can work together well.

It's really a trial-and-error process over time of experimenting and seeing what works in your particular area.

We're talking LOTS of trial and error. :)What I learned a long time ago on forums like this and others when people would ask about what their post card or letter should say for their direct mail was that, "It's more important to let them know what you do and get the message in front of people in need of your service than what the exact message you use is."

PM is always trial and error. 

We say "trial your honor". 

This might be a good place for trial guests until you go live, but you only renting to them is a mistake unless you are not in it for the cash flow and this is truly just a second home that you don't need to make income on. 

While we trialed a bi weekly cleaning service, minimal difference was noticed as our tenants do a good job of keeping the place clean.

I did the free trial on Hospitable - I really liked their messaging features.