Her insurance wasn't that great, but it did knock out the remainder of the mortgage (which she was behind on due to a horrible car accident).

Having been in a car accident that wasn't my fault and the other party trying to extort my insurance company anyways, with my insurance company declining to pay them anything, which then resulted them in suing me instead (though they insurance company had to pay for my representation, though they didn't tell me that, my Personal Injury Attorney Uncle did), I know first hand insurance is not 100% fool proof (though I won the case and they got nothing...This time).

Painting the wall didn't even occur to me, although this is the most cost- and time-effective measure to make the place to look "decent enough" to get it rent out and move on to other one.

Insurance doesnt keep you from getting bugs in your teeth, and a windshield doesnt pay the bill if you have an accident.

"He is young and just getting started" and so are you,not a good combination,quite frankly.Blind leading the blind situations can end in disaster.Are you sure he is licensed,bonded,and fully insured to pay for all damages and accidents?

Did many of those who have done wholesale deals visit with a real estate attorney to ensure they don't get trapped into owning a property on accident (if they can't sell it to a cash buyer for some reason)?

Once those two things have occurred, I suspect the easy money will have been made. 

I have just started doing deals on the east coast ( 3 years ago) were titles are MUCH older than out here in the west coast especially recent lot block subdivision type properties.Very common occurance for us these days I have 2 going now ( quiet titles) for the same reasons some relatives were not notified they need to sign off.. of course they can't be found and are probably dead.Seller inherited property.. old owner never bothered to get divorced or probate estate etc.Not sure the value of the asset in question so the value proposition is very real.

He is very wealthy so does not care about pushing yield to have more problems occur.

When the sale occurs, it's over.