Best family ski trip location?

Snowmass.

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My favorite places to ski are Steamboat, Winterpark & Keystone. They are affordable as well for families.

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We’ve looked at Winter Park and Keystone both looked great. Trying to keep the stay around $3-5k, lodging, skiing, entertainment, etc.

Keystone is a great setup for families. Look at River Run Village, it is steps away from a gondola and has food/shops nearby as well.

Which town is more like a Hallmark movie / 80s ski movie cool mountain town?

I can't seem to figure that out.

Time of year OP? If you are going outside of the peak snow times of January and February, you want to STRONGLY look at the peak snow mountains. In other words, if you are only going on one ski trip a year its not worth going somewhere that might not have decent snow.

That said, are you looking at ski school for the kids? I'm assuming every mountain has it? I honestly don't know? Its $150-200 a day per kid for ski school but you drop them off and for the most part they love it. You can't remotely ski as adults with 2 kids under 5 that have never skied.

Under any circumstance, and depending on the size of your family, $3k will be tight but doable and $5k shouldn't be an issue (although limits choice of mountains).

However, now is a great time to start planning.

If you need gear, there are some great "winter in July sales" going on. You can deck yourself and the family out for a moderately reasonable price - Mountain Hardwear is always solid for occasional / new skiers. Also a lot of summer savings on lift tickets - by way of example, looks like Steamboat has a 3-day "Mid Winter 3" discount for 3 lift tickets for $199.00. That is solid!

Ski school is also an added expense that needs to be considered. As far as accommodations, I'd try to get a cabin that you can cook in to try to save some dinero. Feeding a family on the resort gets pricey.

Steamboat, Winterpark, Keystone, Snowmass and Breck are kind of your options here. Good family destinations.

I just cannot stress it enough - book early!

Keystone isn’t actually a town itself. Keystone is just the ski resort. There is nothing outside of river run.

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He’s a new skier himself. He’s not going to be doing anything but beginner and easy intermediate slopes if he wants to enjoy himself.

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Certainly. I simply meant don't go to Vermont for a late spring break ski or go early to Colorado. Things like that. I don't mean not good enough snow for the back country. Peak ski season isn't that long but many places will try to get you to go in early December or April. I don't mean just for great snow, I mean so that you have good snow and can enjoy it on and off the slopes.

Breck. Ski School for everyone.

Go to Crested Butte, Co. When you are skiing for the first time, crowds and lift lines should be a concern. Any resort off of I-70 (Vail, Beaver Creel. Keystone, Breckenridge, etc.) will be very crowded, especially in January and February. The Denver crowds can't get to Crested Butte (too far to drive). You can fly on Delta or United direct from DFW or Houston to Gunnison and it is only a 25 minute drive from Gunnison. Steamboat is also off the beaten path, but expensive to fly into. The drive from Denver to Steamboat is also pretty sporty in January/February. If you aren't used to driving in snow, don't do it. Crested Butte is very family friendly and reasonably price. Lift tickets for kids under 14 are very cheap compared to other resorts. Crested Butte has great restaurants and try to stay on the mountain (ski in/ski out). You can call CB Resorts and get 1 price package deals for airfare, housing, lift tickets, ski rentals, ski school, etc. My kids started skiing at CB at the age of 3 (all are over 25 now) and are great skiers. Back in the day (the 1990's), kids skied free with an adult lift ticket. Then, in the early 2000's, kids paid their age for lift tickets. Not sure what you pay now, but you can bet it is reasonable compared to other resorts. Oh, and the mountain is very big and has great beginner and intermediate runs. If you are game, they also invented extreme skiing in CB. I've been there over 25 times since 1986 and we mostly drive from Waco (about 12 - 13 hours each way), but have also flown on several trips.