Prospective tenant has two tiny dogs and a German Shepard service dog.

Compared to what you did which was househack a small  multi and the absolute best way for someone to buy their first property full stop.while there will be sub to deals out there they will a a very tiny fraction of the RE market as a whole so your fishing in a bucket instead of the lake..

DADU's and ADU's are 50% of our investment strategy & Glamping, Airbnb, Tiny Houses, Yurts, and Unique Stays are the remaining 50%.We push off market deals in both of those niches - I'll get you on our DADU list.

We've LandHacked 7 acres up on Stevens Pass and have the property decked out with a Yurt, Tiny House, Historic Schoolhouse, and more to come, rented on Airbnb.

You will start to pick up even the tiny differences in how they look at something but those tiny differences often have a profound effect.

In North Park, TINY 2 bed / 1 bath SFR's (with very minimal lot space) START around $550K and quickly go up from there while your small 2 unit duplexes will start around $700KHope this helps. 

If the property is worth enough for you to give a truck and $1000, (which is tiny dollars, admittedly) then isn't it worth checking to see the headaches you might be taking on.After all, if he's willing to let it go for so little, isn't it possible there are serious issues with title?

@Rob Fegan so problem with tiny markets is two-fold (as I see it): (1) you have very limited pool of competent property managers who will manage the property for you, and (2) liquidity of the asset is further constrained given that it's a secondary (at best) market, with a very short list of buyers, should you decide to sell this thing at some point down the road.

Funny thing is I called the agent about another property on the street with student rentals already there but the rent was very low since the rooms were tiny.

Just seems like when you're living in HCOL, owning/renting 4-5 homes in tiny cities in the midwest just won't pay your own mortgage.