OR do I just say I am being too greedy and work on my current deals and pass this one up and forget about structuring $5k worth of private money or the hefty price tag of a HML?

Also, my PML will be on the loan/title with me until we refi and quit claim. 2).

Title insurance claim.

They are 2 separate transactions, with separate costs.You could possibly save on some of the small title co. admin costs, but I cant imagine it being more than a couple hundred bucks

Since I’m using conventional financing I was worried about a foreclosure auction since it might not allow enough time for the title & appraisal needed by the bank,and I would be competing with all cash buyers who would win against me.

However, you contact the title or escrow company and they may be able to provide you with one.

Some attorneys and title companies don't like quit claim deeds, so have them prepare the deed they will insure in the future. 

This title company’s settlement fee is $1200.

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The issue of course is that you cannot take title to your new property before your old property sells - you can't buy from yourself.