For example, a home that might appear ok from the outside could need thousands of dollars of work or might even need to be disposed of... which typically costs $1200- $3000 just to get rid of it.

Literally everything.

I tend to take things literal...Does "Colleague" imply some level of mutual familiarity?

I started out with literally no money and essentially in the same position you are in.

While it is not one specific story and I don't have any deals where I have made thousands of dollars or really high profit margins, I have definitely had a lot of success.  

But the inspection unveiled problems worth hundreds of thousands.

Partner Approval, cash w/ financing contingency, inspection (but not a cert inspection), etc. are used that literally state you can terminate the contract for any reason under the sun. 

I can afford some difference in my calculation, but I can't afford a multi-thousand dollar swing, so I'm trying to educate myself here.

Also you are now joining thousands of such buyers and are a few years late to the party.

He now owes us thousands and is (surprisingly) paying us monthly installments.