Are there upgrades that would help in easing some of the various "complications" that may arise while renting?

I know this is a complicated deal, I hope I clarified things.

Yeah that is quite a complicated one you have there.

VRs (and I'm assuming we are not talking the traditional beach or cabin rental) require a lot of day to day work, more money upfront, higher management and maintenance fees, varying degrees of complications and regulations depending on where you are.

The other loan is an interest only loan they gave me to do a flip that i have finished but wound up renting immediately after i finished (complicated and a story for another day).  

Drawing out the refi might complicate another purchase I'm contemplating.

I own out of state rental property in NY and will have a semi-complicated tax season as I've started my own business, will be harvesting some gains/losses, moved, have multiple W2's, had a child.  

Anyway, for someone in a similar situation but without the non-compete complication, here's a successful idea that I have seen a local entrepreneur do:https://www.tripadvisor.com/Restaurant_Review-g609...As you can see, there is minimum lot development on your part if you can find a local restaurateur interested in a similar set up. 

Still keeping an eye out for other developments, but limiting the size a bit to make things a little less complicated. 

How complicated is the process for a first timer?