Time for new boots. Any advice, especially up in the Seattle area?

I am nearing 50 years old and have had my current gear for the past 20 years. I probably went close to 7 or 8 years without skiing during that stretch, but have been going 3-5 times the past few years now that I got my kids into it. Are boots based on skill level or what you use the for the most? For example now, while I can ski just about anything, I pretty much always stay on the groomed runs and just want something comfortable.

That being said, obviously I am not just going to go into a store and pick out something on my own. I think I got my last boots at Sturtevant's and I remember they even made some adjustments to them years later for free. They seem to have that progressive sale around this time of year because I bought my kids some stuff a couple years ago. Does anyone know if they are still good at picking out boots for you, making adjustments, etc.? I don't want to spend a fortune on boots that I am going to use less than 5 times per season but if they are going to be comfortable, is it reasonable to find something for under $500? I am just realizing how bad my toes hurt and that it rubs a little on that bone at the bottom of the ankle with my current boots.

On another note, even though my skis are just as old, as long as they are in good shape, am I really going to benefit much from new skis? I figure the boots are most important as at least they will make my feet comfortable. The only thing is I am probably 30 pounds heavier since I got them and they don't seem that stable when going fast and straight, but maybe that will motivate me to lose a few pounds :)