Dan, you should probably just go for a good quality boot and forget about new skis/ bindings. You might need to spend upwards of $700-800 for new boots with a good boot fitter setting them up for you so that you can ski comfortably all day. The best skis in the world will not help you if your feet/legs are in pain due to ill fitting boots.Look though the threads on boot fitting on Epic they will give you loads of info of where to get fitted. Next step is to maybe look into some lessons to see if you are skiing inefficiently , this uses lots of energy and gets you little reward but potentially lots of pain.
A good quality well fitted boot will make even mid level gear work well. Bad boot and/ or fit will give you nothing but problems be it pain or sloppy control over your gear. It sounds like you really want to stay in this sport and with spending upwards of $75 for lift tickets at ski areas it makes sense to have the proper equipment that lets you get as much as possible out of a day of skiing. As for where to get this done if your on the east coast Green Mt Orthodics in Stratton, Vt and Northern Ski works in Killington, Vt have done good by me.