(I know it would be a legal disaster if the property goes to foreclosure and the person he sold it to, loses the house and of course sues the borrower for being stupid).

. - You have no recourse against an agent or PMC once you pay them for the placement and it turns out to be a terrible tenant:(If you have the time and network and post here for assistance, it's always a good idea to learn the rental business from the "ground up".Of course, one mistake can also cost you thousands of dollars.

Do know of any resources (books, courses, YouTube videos, etc.) to get educated on private money lending?

If the unit is empty and the potential tenant seems great, I would let them move in on the 29th or 30th of the previous month since most tenants will prefer to move on the weekend and I won't ask rent for those 1-2 days (of course utilities have to be in their name, etc).

For example, intro's to people here that can help you with certain specialties, planning, feedback on neighborhoods, financing of course, etc.

To ty Coos county and Bend together brought back memories of a trip I took in the late 90s when Bandon Dunes first opened.Friend of mine in Santa Rosa has a home at Cross Water and a hanger there at the airport and of course a nice turbine twin to put in it.We departed SR for Bandon  played golf that day spent the night at  Bandon dunes  got up early  played 18 holes at Bandon again jumped into his bird flew over to Sunriver got there by 12  teed off at cross water at about 1pm and played 18 holes there.. so may one of the few 4 somes to ever play Bandon and Cross water in Sunriver on the same day  LOL..   

If your unit doesn't stand out in other ways considering adding amenities like a hot tub, backyard mini golf course, making your airbnb dog friendly, etc.

Of course, happy to connect you to local agents if you want to explore possibilities. 

Of course, all channels can work.. from seller financing to foreclosures.. but from my 30+ years in real estate, I’ve found focusing on cash flow analysis tends to pay off more reliably.So here’s the big question that might help steer your next steps.. what do you think would make landlording less stressful for you.. a property manager, or maybe a smaller property until you get more comfortable?

Of course, nobody forces you to tell a potential partner to tell the truth about what you're going to do with the proceeds of the sale.