Everytime I log into into my KDE, while using my wireless card, KDE never automatically connects to the network. I always have to right click on KNetworkManager, and select my network. Then it prompts me for my router password, times out, then prompts me for it again, afterwhich it connects and life is good till I reboot. I don't use Kwallet, although I suppose I could if you told me that all my problems would be solved by doing so.

Is there anyway to setup my wireless to connect automatically (maybe before login to X) and/or is there any way to stop the need for typing the password twice (it's rather long)?

It would be helpful to know your distro and perhaps more data such as the version of the KDE desktop environment.
I use openSuSE 10.X and there are two options to run the wireless card. The one which you are using is through NetworkManager - helpful if you are accessing the Internet through different wireless networks and/or want to see the network, and the other is through ifup, useful if you are accessing mainly through one wireless network. (My wife prefers using ifup except when we travel.)
If you use KwalletManager it will probably ask you for your password when your operating system loads. However, you shouldn't have to reenter your password for the Wireless Network each time.

I hope this gives you some help.

Sometimes wpasupplicant can timeout before you router responds (if you need wpasupplcant to access you network). You could try changing the setting in /etc/wpasupplicant/wpasupplicant.conf to see if it makes any difference.