Two calls to hire someone to manage mowing and snow; and another to manage operations it would truly be Passive.  

I can't do anything myself besides paint, so I hired a contractor because my real estate agent recommended that he could do alot of things and would be cheap.

I agree, hiring a real estate attorney would be the best way.

A situation happened to me recently (my fault completely), I hired a landscaper, did not have a full contract into place and just had text threads between us..

having just you repped is fine in my opinion but the dual sided thing with an actualy listing contract gets a bit dicy for me personally.

As a new STR investor, hire dynamic pricing to help you manage revenue.

Hiring a property manager to oversee things can also be a big help.

Once the rep helps you with this, then you ask for their supervisor (since they make more money on having calls transferred) and promote how well that rep helped you; then, you ask the supervisor for the same thing.This was told to me in a seminar (a guru one at that); however, this is dependent on your personal ability to not spend the CC's.  

Am I required to hire an attorney to write up the contract and assist with the closing?

I called the 1 800 number and was told they place victims in housing and find re-location housing for  company new hires.