REI is an excellent source for good outdoor clothing and gear. You pay a one-time fee (I think it's 15.00) At the end of the year you get a rebate(usually 10%) on any full price items you've bought. Their own house brands are excellent quality, and they also have an extensive selection of brands like Mountain Hardware, Marmot, Columbia, etc.
Also, you should follow the daily deals at
SteepandCheap
They put up one deal at a time until they've sold out or reached a time limit. They have a lot of incredible bargains on gear and clothing. The site is run by backcountry.com, which is another site worth checking out.
Modern materials have made a big difference in staying comfortable on the slopes. You no longer need to wear bulky, restrictive clothing. It's all about layers. Invest in some really good long underwear (Hot Chilies or something comparable). A selection of microfleeces and fleeces will allow you to tailor your mid layers to the current conditions.
For outer layer, there's 2 ways to go. What's known as "softshell" is the most comfortable in most conditions. They provide a decent amount of water/wind resistance, and a high degree of breathability and moveability. If you plan on doing most of your skiing when the weather is nice, you might want to go with something like that.
The more traditional hard shells consist of materials like GoreTex. They will keep you protected in the more severe conditions.
Also invest in some quality ski socks. They do not need to be thick and bulky. You do not want to wear more than 1 pair at a time in your ski boots.
I'd highly recommend you get yourself a good helmet. The ones these days are very lightweight and comfortable. I find mine more comfortable than wearing a hat. They also keep your noggin warm, and most have adjustable vents so they'll be comfortable in cold and warm weather.
Pick up a thermal face mask and neck gator. Your face will thank you on the chairlift when the wind is blasting.
For your hands, mittens are warmer than gloves, but that's a personal preference.
If you have one of those 1 piece outfits that were popular back in the day, feel free to wear that...especially if it makes you look smokin' hot. Just be prepared to hear the phrase "Hey Lady, nice fartbag!" on every lift ride. Trust me.
You want to avoid wearing anything cotton while skiing. Cotton will not wick away moisture like the high tech synthetics, leaving you cold, wet, and miserable...or worse.
Another warning. Wearing a Starter jacket will subject you to ridicule on the slopes. "Gaper" is not a compliment.
My most critical piece of advice: Purchase a really comfortable bed and pillows for your guest room. And a bunch of foam earplugs for you and your family. I tend to snore rather loudly (or so I've been told)
