This all depends on 1) your input costs versus 2) your projected revenue for the 6 months.

So a nicely decked out  cabin I bet would rent real well for STR purposes  Not sure about permits etc..

I will say they appear to prefer to work with me via email versus over the phone as I set up an appointment with my assigned customer service agent and she cancelled the appointment.

While margins may be equal or higher on cheaper deals, you need to do more of them to yield the same cash output versus one successful larger deal.  

The core market (hole of the donut) is booming and lots of young people moving to the city center and new apartments, condos, restaurants, amenities etc.Alot of the sun-belt is experiencing alot of net-migration...versus at least some cities in the Northeast not so much. 

Trying to go to companies directly is rarely going to be your best bet. 

I like how you point out the "technical" elements at play by mentioning the demand for MBS versus treasuries. 

I am unsure what case law there may be regarding STRs with regards to "public accommodations" versus a typical rental arrangement.

It looks like networking and meeting people will be my best bet.  

This way you can sell land anytime versus if it is under a farm lease or if the farmer paid the cost to seed.