Demand for Midland will always be there, not sure on STR rules but if you're traveling regularly then STR it and get the tax benefits/utility from it but make sure you're not violating the occupancy stays.

Regular rental rates would have been more like $2300. 

the "regulars" who have their turf battles (or hmmm, ya think anyone might ever cut any backroom deals on who goes after what?

Do you regularly work with cash buyers on off market deals?

I understand that people like face-to-face interactions.

It looks like your seller wants to seller finance the deal to 'be the bank' - which can be great - maybe you can negotiate a better deal on interest rates than what is currently going on in the regular market - which would be awesome.As for which home first - I would definitely go for the duplex you are already in.  

Do our regular rent increase and then add on an extra $100 or $200 because you have to chase the rent Let the tenant know now that their rent will increase significantly if you have to chase them for the rent every month. 

This is especially true the finer the market is.I see a lot of different strategies from serial investors I work with regularly, and would be happy to learn more about your finer details as such.

Attend local meetups regularly.

Backstory:We rent the ADU out regularly via STR or MTR and live in the main house currently and are looking to size up.