This is landlocked property which was part of one of those land sales where a larger lot of woods was subdivided into a bunch of tiny lots and marketed to people as an investment.

I'll be working with an outside agent who is familiar with the area.My questions: Does anyone have recommendations for an architect in Oregon that specializes in smaller homes (think cottage/tiny home) - preferably one that is familiar with coastal builds?  

At the end of the day, taking run down houses and making them nicer so that a family can turn them into a home, brings a tiny bit more order and a bit less suffering to the world.  

Short term rentals, tiny homes, etc?

Not only because of the safety, but because the list of available companies that insure knob & tube is tiny and because they are taking on the 1800's technology risk, they are likely going to charge you for it.The upgrade will likely cost a bit but your place will be more marketable and also, all in all, safer.  

Obviously people are still building and renting buildings despite the fact that Prop 13 creates vastly different property tax rates depending on how long the current taxpayer has owned the building.The biggest beneficiaries of Prop 13 aren't tiny landlords, they are large corporations like Disney.But more to the point, if landlords thought that price stability for small business was their concern then they would support rent control for tenants and not for owners.

They compared California City to Las Vegas and other large cities in the Southwest that began as tiny desert outposts.

You can build a "tiny home" or "park model RV" but they won't be HUD compliant/licensed.

also look up tiny homes or cabin layouts.

Are there any builder websites that might show a # of different property builds that might be optimized for something like owner occupied or tiny multi-family/duplex?