There are lots of things that can go wrong for which you should have reserves.

Does anyone know, or have a good idea, about the difference in returns on entitling & developing the land for each scenario, with final objective to sell to a builder to build and sell the structures him/herself.  

Went smoothly, and he got the deal done.  

Specifically, I’d love to know what resources or tools you use to:Track market trends (e.g., shifts in pricing, demand-supply changes).Analyze local or regional real estate data.Identify key economic indicators impacting the housing market.Stay ahead of demographic changes or migration trends.Do you have any go-to platforms, datasets, books, or even strategies that have been especially valuable?

There are many many pain points to having a large company run your STR, so the reviews should be closer to the bottom of the list. 

I'm going to give a verbal warning followed up with a text message describing what was talked about so we have records if something bad happens. 

Is it possible to sell or refinance one unit to pay the other off completely. 

A capital improvement is not - it gets added to the basis which ultimately reduces the tax due on sale but it’s not tax deductible in the sense in reduces current income. 

Reach out to @Dan Geffen.

I too am confused by the “It won’t look consistent to the tenant or to the accountant.”