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@Asim, I was having V4.1 on my IPhone, and Jailbreaking was very simple..Just type jailbreakme.com in your phone browser, and it would do the rest. Once Cydia is installed, then install "Installous", after that you get all applications you could possibly want.
I dont know if any Jailbreak is out for 4.2, so I am in no hurry to upgrade with Itunes, even though it keeps pstering me to do it.
I am having HTC touch pro with windows 6.5 , but now looking for latest motorola-droid. Still not decided how to break contract with Verizon for HTC touch pro 2