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?

Its complicated, and if you end up with a dud you are done for.Good luck.

That's because if for whatever reason things go south, depending on your jurisdiction, a foreclosure can eat up a lot of capital and time, there's also the threat of federal/state tax liens complicating matters. 

aaron buying notes is quite complicated if you are not in on the origination of them. 

I'll share that we avoid lending on wholesale deals because they can be mind-numbingly complicated compared to the amount of work involved in a simple purchase and sale (REO, probate, private party, etc.), for the identical return.If it is the numbers, I still don't see the problem as your lender not knowing how to evaluate a deal, especially if they gave you their criteria, as you indicated.

@Alicia Ogunmiloro,As @Wayne Brooks points out, notes are a complicated asset.  

It does make the return more complicated though and for straight simplicities sake i know people who haven't claimed it because in the end it usually is close to netting to 0. 2.