If they offered like a $2 or $3 method of tranfering UMD games, I wouldn't mind that much (but not more than that).
WB did a limited time media transfer deal for HD-DVD consumers to switch to BD copies. I don't know how that actually panned out (number of orders processed, etc.), but it involved mailing the sleeve inserts (with UPCs) and paying $5 per movie plus shipping and in return, they sent you BD copies of each movie "upgraded" in this fashion.
I have a stack of games on UMD, most, if not all that are currently available on the PSN Store, but I would mail SCE every one of those disks if I could transfer my licenses to PSN purchases. Preferably for less than $5 a title, seeing as how they wouldn't have to ship me anything in return; just e-mail me a redemption code.
Fact is, UMD is going the way of the Sony MD (Mini-disc for those of you who have never heard of it). I say "good riddance" but won't be buying all my UMD games over again just so I can play them on a NGP.
As for the hope of a "UMD drive" and transfer kit; I'm not holding my breath. If they were going to do this, they would have already done so for the PSP Go, which probably would have improved sales considerably among current PSP owners.