You could have this conversation with the agent and see what happens if you are convinced they did t serve you well.

Then, when the gifts add up enough, get your equity out of prison and take that cash conversion and invest it at that 5 x face value it has outside of those "walls". 

I am currently having conversations with a lender that will work with me on Home improvement loans giving me some options on improving distressed properties, but I will need to ask if they have ability to do wraps.

Pls check w your attorney or find an attorney that is conversant in living revocable trusts.  

I have found some good tax lien leads and I just don’t know how to go about the conversation when cold calling about these properties.

The county records still indicate that it is a duplex but the conversion was obviously done years ago before zoning came into affect.

Consolidate investment accounts and do Roth conversions if the taxes make sense.

I do not know the cost of an ADU in Oregon and you did say you were going to do a lot of the work yourself so I am not saying your numbers are wrong but the cost of a hands off garage conversion to ADU in San Diego starts at $90K. 

I would google "airbnb host forum" and get on a couple of those to start conversations.

Tenants pay utilities.I AM considering for the future a HVAC conversion,  but I wasn't thinking about doing it all at once.