Generally most private money lenders are going to play a lot more conservative but be able to close faster/make a faster decision on lower risk deals. 

The Arbitrage unit that we operate is owned by a friend, so we probably played a little fast and lose with our agreement with her. 

We both lost out to someone that was willing to give the Seller almost the price they were asking because they were doing a 1031 exchange were they had a substantial amount of cash and they liked the property location.This similar scenario has played out for me several times over the last few years because the market was so hot.

You are playing a fine line this close to the extended date though.

For LTR they are expensive so it's more of a appreciation play. 

IMHO they are the worst properties Vegas has to offer although they have tripled or quadrupled in value in the last 10-15 years, that was the play, not the cash flow. 

Gut it out until the end of January with this person and either a) play more hard ball about the vehicle and other stuff b) play it softer and just gut it out with them2.

I’ll play Devils Advocate and recommend paying off the debt first.

Obviously we cannot force the borrower to sign so I said let’s foreclose because I think borrower is playing games.

You are trying to enter ACTIVE real estate investing where YOU play a SIGNIFICANT role.