of thousands of dollars in lost productivity, so the business is likely a lot less price-concerned than other residents. 

Due to item 1, adding an ADU can require years to start achieving any return (once the accumulated cash flow recovers the initial negative position).4) Adding an ADU is a slow process.

I was quoted about $6k to $10k depending on what what products/packages that included what I was looking for.

Slow and steady still wins the race. 

Also, someone with real estate investing experience can probably help you shop for loan products that could be more flexible on the owner occupancy requirements so that you can scale at whatever pace you want. 

They might move very slow though.. 

The best wholesaler and the ones who run it like a business, usually start as productive home buyers.

STR hosts, what's your go-to strategy for filling up bookings during slow seasons?

Home was flipped and I buy the product they sold.

When you do it yourself it will require more time from you and also in slow seasons you might not make much money.