If you are a partial owner of this land, I would not invest much or any money into it.

This is in an effort to let the investment play out and try to minimize their loss. 

Lots of MFs in lots of areas if you reach out, or have reached out, they're all coming back.

Portland is similar.Bend has a ban on STRs in the much of the city.

@Denis Orlov I don't do STR, but I've rented one of my personal properties for arbitrage before. 

I am a wholesaler out of Maryland looking to start content creating on my journey, looking to connect with some people that do the same type of thing.

Whether you’re just starting out or you’re a seasoned investor, BiggerPockets has a ton of resources to help you along the way.

That will increase your material costs for the job and is the contractor paying for the material in their bid or are you paying for it and paying them a labor cost.

I like the fact that one and a half units pays all bills.

I do not understand your remark as related to the DSCR loan.  2 ADUs are not allowed by f/f conventional financing but is not always enforced.Fortunately if you stay with the current tenant without a refi, by the time you pay principle it is likely the rent will have increased enough to absorb the increase mortgage payment.