Okay, here we go.
Skiing. Mt. Bachelor basically is in this natural symbiosis with Bend. The ski resort and the town feed off of each other so much, that it's a bit crazy. Bachy, like most volcano hills isn't the most gnarly mountain (some including myself call it Mt. Flatchelor), and there really isn't a single spot on the mountain where you can send it off a cliff or anything... but it is about 25-35 minutes away, and is pretty fun still. It's large enough to accommodate the crowds, and has some good powder that's actually damn light a lot of the time. When the top is open, you get lots of different types of snow on the way down, which gives some challenge. The runs are fairly long, and the parks are phenomenal. The weather is fucking temperamental as fuck, though.
Other than that, Hoodoo is about an hour out of town for something different (but mostly a smaller version of the same thing without crowds... but cheap passes for night skiing! and an OK park, as well), backcountry in the sisters and crater lake areas are very easy to get to, and Hood is within a daytrip distance.
Biking. Thousands. Literally Thousands of awesome bike trails all over the place. Bend kicks fucking ass for mountainbiking and roadbiking alike. I really don't have to go into it because it's something I haven't fully explored.
Fishing is pretty damn solid.. You can't really beat the Deschutes for fly fishing, and it's the only place where you can pull out Redband trout (unique to the Deschutes). There are also lots of lakes around for other types of fishing.
Nightlife and Bars are excellent for a smaller town. The place swells with tourists during any season, so you meet lots of people, and enough kids go to COCC (community college) and OSUC (growing 4 yr university) that there is a bit of a college presence too (though not very much) I'll use this spot to touch on "breweries/food" because they are kinda part of the night life. Taprooms galore, and Bend has an "ale trail" because it has like 7 breweries right in town. Several have their own restaurants and shit, and holy fuck it's the dankness (seriously... Deschutes brewery for one has become one of my favourite microbrews - and is the only brewery I know of in this country that nitrogenates certain beers - a la Guinness) Restaurants cater to tourists, so they're usually really dank, but can be a bit pricy. There's plenty of variety, however. Go to Parilla for the best value food in town... (also, if you don't have your own hot tub, go to MacMinamins, grab a pint and pay 5$ for the soaking pool they have there. It's like a massive turkish bath, and it's badass as fuck after a day of shredding around
Live Music is alright. They attract about the same as what you'd expect for a 100k person city or so. I can't really talk on this issue, as I grew up spoiled as shit going to shows in San Francisco - Almost anywhere else is a bit of a 'meh' scene. But Bend gets some good acts rolling through every once in a while. They just don't have some large venue to play in or anything.
Women? I'd say the ratio is pretty even... It's a large place though, so I really wouldn't call it a parking lot or anything like most ski towns tend to be.
Camping/Kayaking/Rafting? All great least to my knowledge. like biking, I haven't fully explored it, but it's all either right there or within a manageable driving distance.
Cost of living is pretty average, but definitely affordable if you do it right. Oregon has no sales tax, so if something says its 9 bucks, it's fucking 9 bucks. The dollar store? Yeah.. it's actually a DOLLAR store... you pay ONE DOLLAR and you're done. On the contrary, someone else has to pump gas for you. You can't pump it yourself. It's kinda nice if it's fucking cold out though, so you don't really have to get out of your car and deal with anything - but after 10PM? There's like 2 gas stations open, and they're all the way on the edge of the town and that is the most obnoxious thing for a night-owl like myself...
Job market isn't too terrible. There are tons of businesses in town, but lots of them tend to be seasonal, as the ebb and flow of tourist seasons go by. There's enough grocery stores and such around, though, that as long as you're presentable, and somebody is hiring, you should be able to snag a job. If you're moving there professionally, then that's a whole other matter, but for the most part, it's better in Bend for young folks looking for work than lots of other cities of the same size.
So yeah. I like Bend. Kinda looking at it as a potential destination to move to, soon.
