@Matthew Sarro - It sounds like you've got a solid handle on your finances, especially with no major debts hanging over your head.

• How should I handle accepting rent payments for "extra" time?

That is an issue for the person who handled your closing (ie why did both they and you miss it) to deal with. 

Here is a past post describing the way to handle this. https://www.biggerpockets.com/forums/51/topics/393996-how-to-best-handle-boarder-income

I think one angle to consider is instead of learning how to manage, learn how to own and then adapt that to become a co-host.Something like owners work/hire you to pick up slack in regards to being a "on the ground" person to handle problems.

Systems, processes, efficient, organized, steady, handles all the details.Another model is:1.

Systems, processes, efficient, organized, steady, handles all the details.Another model is:1.

Let the expert handle this and recognize it is the cost of doing business.  

I know people handle the hiring and pay structure of their contractors differently.

You could pay a friend for showing and handle the rest electronically online.