@Erica ArceCould you have a written agreement directly with the wholesaler that outlines your fee for bringing a buyer to their deal?

@Akshay Monga Nice to see that you have such a cushion of money.

Ryan who I met once when I was in Maui is a super nice fellow..

We have had much greater success renting a whole unit out that renting our individual rooms, though it has been nice to have some flexibilty to accomodate travelers who are coming as singlets and doublets.

Code § 1701j–3 - Preemption of due-on-sale prohibitions(1)the term “due-on-sale clause” means a contract provision which authorizes a lender, at its option, to declare due and payable sums secured by the lender’s security instrument if all or any part of the property, or an interest therein, securing the real property loan is sold or transferred without the lender’s prior written consent; 

Nice to meet you Khalid, saying hello from Chicago!

By snagging a house in a nice neighborhood, you will likely command a higher rent for your ADU. 

That said, VRBO doesn't do auto messaging and that's a PIA that makes a channel manager a nice tool to have, but often the cost isn't worth it until you get at least 1 more unit - again, my opinion.  

Ideally I want a combination of the Burnham block duplex style but cleaner, and more usonian looking.

My strategy in Arizona has been adding bedrooms and renting by the room - currently getting 850-950/room in nice neighborhoods.