let's set a couple things straight..
first off, all the updates for the Verizon Fascinate (i500) were done through OTA. nothing was done through Kies.
What model do you have? there's the fascinate, mesmerize, showcase, and the telus fascinate (which is more like an i9000, or galaxysmtd)
also, i believe all of the i500 variants have official Gingerbread of some sort. the verizon fascinate has 2.3.5 which you can get through an OTA or through Odining
but what do you want to update to? do you want to delve into custom ROMs (unofficial firmware, that's how you can get Jellybean running on this phone)? or do you just want to play it safe and go official?