Here goes my first post, I've been lurking in the shadows on this forum for a few months now; I figure it's time for me to contribute.
I'm a proud owner of a 2005 WW LE 3505 (purchased Oct 2012). I'm assuming your buddy is either looking at an LE 3305 (33' version of my TH) or possibly a Superlite version. I can speak to the quality of the LE versions as being of solid construction. DEFINITELY check the roof, especially where it meets the front cap as well as the rear seam since that is the low point of the roof, which causes the water to pool there. If there is signs of the OSB (some call it plywood or chipboard)becoming wet and warping underneath the roof material, there was water intrusion at some point which means you need to start poking and prodding the roof as well as interior and exterior walls adjacent to the possible leak point to look for soft spots.
Let me know if you have any specific questions if it does happen to be an LE version. Also, what does your buddy consider a "fair price" (just curious)?