Rejailbreaking with pwnage question

Hello,

So I jailbroke a few days ago and I was pretty inexperienced with the whole hacking concept. As a result my iphone became laggy, cluttered, and the mods began fighting with each other (if that makes sense) everytime I would reboot my dock and all my icons would be rearranged with blank icons scattered everywhere. I decided to rejailbreak it with no problem but all my text messages got deleted, and that was a problem for me. so I restored and tried again but now it won't let me. It says there was an error with restoring. I'm not sure what's wrong does anyone have any idea? one question i have is when pwnage asks if your phone has been jailbroken before (does it have the pineapple) does it count if it is restored to factory settings (no pineapple, regular logo)? Any idea what's going on?