I live in Dawson City, and go down there often - about once a month,.
It is a small city - about 26,000 people. There are no real shopping malls, but there is a large WalMart and Canadian Tire where most people go. Prices for food are good for Yukon (about 1/2 of Dawson), but still a bit more than down south.
Housing is getting expensive. They are building housing for nurses right at the hospital, but if you've a family, that won't work! Whitehorse is kind of long and skinny. It has about 8 streets parallelling the river, but it is about a mile long or so (BIG guess here!) for the main area, and several miles long overall. There is housing near the hospital (east), and west of the city at Porter Creek.
It is a bit of a rough town. As the major centre in Yukon, by far, it attracts people in difficulty. High fashion is not something you need worry about up here, that's for sure. People dress for the weather, not for looks. There is still a bit of a frontier mentality - much more where I live, but still in Whitehorse too. People kind of do their own thing, and you don't get bothered by it. Some really like that, but it means some of the social graces you might find in a big city are missing. Whitehorse has sort of a "quiet desperation" feel to it. It does not look like a rich city as you drive around in it, although there certainly is money here, and decent wages as well.
There are 2 movie theatres in town, and a couple of good museums. Drinking is a way of life for many - we are the biggest drinkers in the country. There is a selection of restaurants: three (?) Chinese restaurants, a really good Japanese one, a crappy Vietnamese one, an Indian one that I've heard good things about (although the motel it is attached to is supposed to be pretty bad), a McDonalds, and one in the WalMart, and two Tim Hortons. There is an A&W, but that's it for fast food. I'm not sure if there are any "fine dining" places - if so, I've never found them.
It is very much a tourist town especially in summer. It is on both the Alaska, and Klondike Highways, so anyone going to/from Alaska passes through Whitehorse. I do not know what it is like for families there. I should think not bad. All of the Yukon is much like living in a small town - everyone knows everybody, so you soon learn who the troubled kids are - and, if your kid is one of them! Likewise, you learn the good kids too. There is a fabulous sports centre there (a legacy of the Canada Games), which is amazing, and popular. There are also loads of opportunities for kids if they want them. The average spending here is about $37,000 per year per student in the school system. This is at least double what most other provinces pay. There is also the Yukon College here, so kids can at least get started on a University education without having to leave town. I think it might also some degrees as well; not so sure about that one.
It is beautiful here! If you like mountains, hunting, fishing, and the outdoors, Whitehorse is definitely the place for you. I have been all across the country, and Yukon is one of the most beautiful places in Canada. But, don't let the maps fool you - it is a very big place too. Distances are great here - e.g., it is about 2500km to Edmonton.
The hospital is really nice. Big, bright, and new, with more things being added. It is the major hospital for the Territory - I think they are building one in Watson Lake, and there are building one soon in Dawson, but that's it. Everyone comes from the "communities" as they are known, to Whitehorse. E.g., all babies are born there. All specialists are there, and so on. It is really the hospital for the whole territory, not just the city. Major cases are sent to Vancouver, or Edmonton. So far, I've been pretty impressed with the level of care here though. E.g., the high numbers of natives (1/3 the population) means a lot of Residential School survivors who suffer from PTSD - especially an institutional setting like a hospital. But, the people there are caring, and understanding, for the most part.
It is hard to attract medical people to the north for some reason - perhaps the big unknown. I understand the pay is pretty good - costs are higher here (gas is about $1.12 in Whitehorse, but heating can easily be $800 per month for a house in winter). But, not horribly so - the WalMart meant prices everywhere dropped quite a bit when it opened.
So, think of Whitehorse as a small town, with a few stores, not a lot of nightlife, tremendous opportunities to get into nature, and a chance to make a real difference in people's lives - your patients will know you by your first name most likely! People seem to either love it, or hate it here.
I'm one that loves it!