Looking to get some quotes from local handiman/contractors to get this thing back into using as a comfortable addition to our modest house and possibly renting out as an Airbnb.Who's got recommendations/referrals in the greater Seattle area!?

These are professionals with additional training and a stricter code of ethics.

There is an "insured" and an "additional insured", and someone mentioned that you can only name one of each on the policy for insurance company he use.

Live in one unit and rent the others, this would give you additional units without extra mortgages, and help scale your business quicker. 

Additionally, if you have other advice or suggestions, I'd welcome that as well. 

If your goal is to keep the existing renters and rent out individual rooms on AirBnb, then you would be required to follow some additional rules.   

There is the possibility of expansion as we are going to get about 15 additional Acres that have not been developed yet.

As someone else stated, banks will want to see a couple of years of rent roll typically , so do a solid job of estimating the current rents for those units and what additional CAPEX is required, apply a 50% rule and CAP rate for the area and that’s the value.

The home is 2,300 square feet and has an addition on the back that was not touched. 

So its not a additional amount I have to pay.