Maybe if you had a bit more experience on typical contractor shenanigans , you could have gotten through it or if the guy wasn't questionable and got you through it, it would be singing a different song.  

I likely stand to get some sort of inheritance from him someday, and I think he'd roll over in his grave if I used it all for down payments on multiple properties with mortgages and leveraged up to my neck.

Some we sort know each other.

The typical method of going through a real estate agent and using MLS doesn't seem like the ideal path (if only the easiest and most typical).  

You typically have to pay a 3% balance transfer fee, so transferring $28,000 for example, you pay $800 or so, but then the bleeding stops and you have between 12 and 18 months (depending on the offers) to pay with zero interest charges. 

typically, contract law dictates that agreements for one year or more must be executed in writing. an email response is likely not enough to fulfill the requirements of an executed contract

I have seen a TCB sale in a different county overturned by the TCB because there was a court order to postpone the sale, and the TCB did not postpone - that is another sort of screw up that the TCB will perform ;)This sale might have been under the automatic stay of the BK courts - so the TCB would not have been allowed to sell, and it should have been postponed if that is the case.

I am considering making a deal on a house that will be a sort of blend on seller financing and a lease option.

I really don't want to fall into the typical stereotype of the newbie who wants to wholesale and then flip and then accumulate rental properties, even though that is true I want to solely focus on wholesaling for a while and really master it.

These actions typically drag in the seller, agent, and broker....It may be easier to see if you can settle with the previous seller/agent first.