.) • Give/donate each away-----I expect many here have already been through similar dilemmas and interested in experiences, lessons learned.

But to be fair, I have spent a great amount of time very recently trying to help another professional 20 years in experience ahead of me bail out of a mistake I NEVER would have made.

Chalk it up somewhat to their inexperience!

Part of my issue was not having a reasonably priced handyman ahead of time and eventually overpaying to just get it done and also inexperience as a manager.With that said, you essentially have two options: very cheap properties in less good areas (you're looking at 100k or less--which you might have trouble getting a good lender for)  or trying to do some sort of house hack (e.g. live in flip, live in rent by the room, multifamily) where you budget will be closer to 200k-300k.Personally, I would not look at real estate until you are maxing out your 401k and IRA, but lots of folks have done significantly better with real estate than stocks and would think I'm crazy for suggesting this.

Inexperience all around.  

I'm curious if others are using structured surveys for tracking trends in experiences.

Oh, you didn't have to state your inexperience, it was obvious. 

But even with that, he needs someone to guide him or JV with him who isn't going to take advantage of his youth and inexperience.  

That’s sounds like inexperience and lack of knowledge about other markets talking.

In my almost 20 years of doing Subject 2's and working with other investors in almost every State in the US, in the very few instances the Due on Sale is called it is because if the inexperience of the Investor in not knowing how the transaction is to be done, (not closing with a Title Company or Attorney, not doing the Insurance correctly)Most of all, (not communicating with the seller) Bank calls the Seller to offer them Life Insurance or some other service, and the seller tells them, "I don't own that house any longer, some guy took that house from me and put some renter in it"If you dig into any investor that tells you they had a property or a friend of their brother in laws Collage roommate that had the Due on Sale clause called, you will most likely find that the investor screwed up somewhere.This is why Education and knowledge is needed on any Real Estate transaction.I get calls almost everyday from someone who screwed up on a Subject 2 and is asking to be bailed out, many times they do not want to pay for help, and things just get worse.If you know how to make the Bank Comfortable with the transaction, all is good.Last year I had a couple of hedge fund managers call me asking how they can offer their under preforming loans to Investors to by Subject 2, wow what a great deal, I could call Pace and he would have buyers the same day for a 1,000 homes, but the legal aspect of this would hold the Hedge fund liable so we could not do a deal.