I got my first boat this way. Although the seller wasn't all that forthright in telling me so... I was naive and didn't think the seller would pull my leg when he said he owed the bank $34K but would sell to me for $31.5K and eat the difference. It was only when I called the bank six weeks or so later wanting to know why they hadn't sent my title, only to find out my seller still hadn't paid off the balance of his $44K (not 34!) loan that I found out that he was short selling.
The bank did end up approving and I got my title, but there was a night or two of cold sweats over it.
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