He lived there for just over 4 years and was a great tenant that I was able to confidently refer to the next landlord when he moved into his next place.

Probably an appraisal, if you're not 100% confident of valuation.You'll also want a closing agent (a title company or closing attorney) that has done a fair share of land contract closings.

We should see a little more inventory once the lock down ends and sellers find the confidence again to show their house to buyers.

The market that works best is where the numbers make sense for you, where there is a large tenant base so that your house does not sit vacant and finding the team you are not only most comfortable with, but also have the most confidence.

This tenant has done this before, I feel confident.

@Alek Suarez I don't think that anyone can confidently say where housing prices are going to go. 

Looking back I am still confident of the decision and have 1) outperformed the 401k, 2) have control over assets, and 3) am much more tax efficient.  

I think some people get their RE license as a way to understand the industry or as a confidence building badge of honor.  

Well, I am fairly confident that, if purchased at the right price, STRs will make money in this area. 

That said, if you are confident in your own strategy going forward and do the math with scenario planning it might be a good option.