[GTang]

I have been thinking about jailbreaking my phone for awhile now, but I have a few questions. There seems to be a lot of jailbreaking programs out there. Out of all the free ones, which ones are the best? Do they have their own pros and cons?

But importantly, what about my contact lists and text messages? Some of them have conversations that I want to save, will they be transferred over? Can I do that?

[cpjr]

All your info including contacts and sms's are saved when you backup the phone in itunes.

As far as software....its either Pwnage (Mac) or RedSn0w (Winpc)....both have extensive threads on here with instructions, etc. And both are free.

Welcome to MMi.

[blkcadi]

Welcome to MMi
I'll admit there have been some problems, most have been user error, no setting up as a New Phone, etc.
After the jailbreak is complete you can sync to iTunes from a back up and all your contacts and stuff will be there.
More info about Mac/PC 2G/3G will be helpful in getting you the correct info you need.
Here is a guide that will show you the process.

Well, I see that cpjr posted before me. you'll be fine