At this stage in my life, these equity plays are more impactful than holding onto a property for a couple hundred dollars of monthly cash flow.What’s your take?

Usually all you need is a couple really good comps to know how your property would do and that is easier to find with a paid version of Airdna. 

I have financed a number of STR properties and they will usually be appraised as a pure real estate as vacant value and a cash flow adjusted commercial value, sometime separated as going concern and real property.  

My sample size was just a couple hundred but it seemed to be as accurate as propwire which I was trying out for skiptracing.

Its relatively easy to manage the process once you do it a couple times.   

If you go to sell the business, but want to keep the land and lease it to the business, I would then separate them at that time. 

So get a couple of hundred there (after HOA & note). 

Tenants in many markets already believe they pay too much (contrary to recent studies that show rent to property values have never been lower for the large US cities).If my insurance costs are not double my current rates over the next couple years, I will be pleasantly surprised.  

HI,I was curious to hear from other professionals, when you have a tenant for a couple of years, and then he wants to add a new person to the lease, what steps would you take?

I have taken a couple of Joe's courses (free and paid) and found them very helpful @Joe McCall.I can't recall the price, but if it was $500 or $1,500, it was worth it to me, as I learned a lot about marketing in addition to lease options.