Portable Media Players Questions & Answers

I`ve been struggling with this update for several days now, so I`m looking for help. The system I`m using for the update is Windows 7 64-bit. The ipod`s firmware is ver.1.x I`m trying to update to 2.x or above. I tried using the standard way which is connecting with the original cable (as crossblade suggested in one of the other threads) and updating through iTunes but it keeps giving me "Could not open key" which as far as I read is a windows registry problem. I read that it is ok with older versions of iTunes, but it didn`t work either. I tried recovering "baked" backup but the device bricked and I had to unbrick it(I`ll share how if anyone is interested). I also read that if i jailbreak it i can use fwchanger and probably the iTunes will update. I ran out of ideas have anyone else faced this problem and is there any other way besides jailbreaking that I can use.
Thanks in advance.