And someone jumping into this as a complete newbie can expect that they have a decent chance of making some expensive newbie mistakes.

Typically the latter is the one I would rather invest with, as they are first acknowledge that they failed, and therefore have a chance to learn from it.

I am so full of regret for even giving them a 3rd and 4th chance.

If the proposed loan is too risky because (1) chance of default is too high and or (2) cost of foreclosing too high or time it takes too long and we would otherwise decline the loan, we might offer to purchase the subject property for a price equal to the loan amount.  

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

Hey @Cameron Wells so the tiny homes on wheels are not real property, they are essentially RV's.What I would find out is what the property is worth bare.

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

You may find a deal for yourself to own but I'm not sure how many you'll have a chance to wholesale.

Point being that property you acquire 1-2 years ago is likely to be subject to deferred maintenance and capex, so their "long term" performance in rankings 1), 3) might skew poorly in year 1-2 but may pickup  after you've found and fixed all the hidden issues.I know if i did this exercise across my portfolio, the recently acquired ones wouldn't be fairly "stacked" because of all the year 1-2 cost build up from what the seller deferred, but have good chances at being future performers in years 3-5.Maybe that's why you have 2) and 5) but curious your general thoughts here are for evaluating this. 

This is your one chance to change things.