Well I pulled out my 256mb pi and plugged in the wifi dongle with a clean install to try and get it to work.
I did all the updates and firmware updates, then instead of the built in wifi manager I gave wicd a try. Lo and behold it worked perfectly on the first try.
I went ahead and tried wicd on my pi connected to my RepRap, and after a few changes to what I had tried before to get my wifi to work I was able to get it connected as well.
So I think I'm going to do a clean install and document everything with wicd instead of the built in wifi manager, and I'm also going to see if I can optimize PrintRun a little more. I think that it's not displaying the gcode correctly, but I have a feeling it's still parsing everything in the background and using up memory.