Well, while my head is still spinning somewhat, I do appreciate all the advice and it makes some good sense. I'm not sure it's bad technique, because up until he took a few years off he was a much better skier than he is today and his knees were bugging him back then too. I think it has to do more with 10++ years of skiing, mountain biking, soccer & mixed martial arts that just took a toll on the poor guy.
I'd say he's a medium turner right now, nothing too wide, but nothing short and fast either at this point. Likes places like Magic where it gets naturally bumped out, but also likes his fair shair of groomers. I'm sure I'm selling him short though, I'm probably not one who should be judging other peoples' techniques.
I think after hearing this from you all, I'm going to take him out to some demo days (think there's 1 @ Hunter on the 8th?) and then if he finds something he likes try to search for an older model of it. I'd wait until end of season to grab a deal on this year's skis, however, I'd find it a miracle should his current skis happen to wait that long. If I'm going to be taking him out every weekend with me (which is my grand scheme, and he also seems to be ok with this for the time being) I'd like to have him in something a bit more reliable sooner rather than later.
I don't know about any places on Rte 20, so I don't think it's around anymore. There's a place in West Springfield & another in Holyoke but to tell you the truth, I'm not such a fan of either. The owners of both places have used car salesman syndrome and seem to want to stick you on whatever you're willing to pay the most money for (when I was searching for skis I told one of them I had a budget of $400-500 and he immediately redirected me to a group of skis in the 1000 range).
Thanks for the input, everyone
I will throw both of those skis back into the perhaps pile and continue my search.