The Streak is available now unlocked with Android 2.2. You can get a preview if you search for "Dell Streak Android 2.2 (Froyo) update review" on Engadget (not sure if posting links is allowed here). Landscape homescreen has been added.
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That said, both are about to be outdated again soon with Gingerbread.
I'm not a fan of Touchwiz (esp the app drawer icons) so hopefully the Nexus S rumors are true because the screen is very nice. I would forgo most skins for faster updates.
Gingerbread was strongly rumored to be a user-interface update - Froyo was claimed earlier this year to be THE final performance update - fwiw. (Never say never and time will tell.)
Some people like to root and remove themselves from the vendor-approved update schedule - others like to stay more conservative. It's preference, there's no wrong way.
I've owned good and bad Dell and Samsung products and don't have a strong opinion on the makers (I do lean in favor of Samsung, though - seriously - the Captivate is a variant of the Samsung Galaxy S - it's their world class phone).
I do have a strong opinion about the performance of any Android 1.x vs. 2.x - going from 1.6 to 2.2 will blow your socks off.
Over in Evo land, many of us were blown away by 2.2 - others honestly didn't see the point and went back to 2.1 and were happier.
I'd say - try each one in the store - just fiddle with it for overall feel and trust your gut. Make them give you a 30 day return/swap guarantee if you can, so if you don't like one, you can go for the other. (I don't know if AT&T offers that these days - and expect a restocking fee if they do - no free lunch.)
Best luck!
