We went forward buying houses in our own names until the point where our DTI got out of balance, and where the reserve requirement was higher than the next down payment. 

.#2 - Start going to events like those at Home Depot on Saturdays, where they show you how to tile, or other basic trade tasks. volunteer to help friends, volunteer for a Habitat For Humanity project.

. - Feasibility & Permit-ability: If you know where to look you can still secure a STR permit in most cities or counties from Brookings to Astoria.

For sure seems like a situation where finding the right place is essential. 

The jomax location has more of a rural feel where lookout mountain is completely built out.

I'm talking about the open-ended interactions, not situations where you've specifically spent your time for an individual. 

At this point I think the best ADU strategies are applied to 5+ unit multifamily properties where the lenders look at rental income for property valve. 

I did a home improvement project where one of the perks was 0% for 2 years.

Depending on where you are, do this half a dozen times and you could have $500k-$1mil tax free in a decade or so. 

Where in the mid-west are you getting props fully renovated for 55k that you can flip for say, 80kish?