Does It Bother You That Obama's Middle Name Is Hussein?

That is true. But Hillary is a known commodity. Her defects have been in the public eye for almost 2 decades. And there isn't much chance the Republicans have in defining her like they do Obama.
With hillary Democrats give themselves a fighting chance - a replay of 2000 and 2004. With Obama the risk is a blowout loss, and at the same time a blowout win.
I guess you can look at it as an insight to personality. Between the two I favor Hillary, and I almost always hedge my risks.

I'm a lot like you in that I always hedge my risks.

The difference is I see Hillary as a sure losers. She has way too much baggage to be exploited and unlike Bill she's not good at brushing these things off.

Obama on the other hand I think gives the Dems a fighting chance because the only really things to attack are cultural. Also, with cultural things you run a 50 - 50 on success. Sometimes they work, sometimes they back fire. The Clintons learned this as it backfired brutally on them trying to play the race card. With Hillary's scandals and high degree of personal conflict it all sticks 100% of the time.

I see Hillary as being a sure fire loser and Obama as being a possible winner.