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What an awesome town.
I've lived here for 2 years now and can sum up the city from my experience with the following:
1. Bend is an outdoor enthusiast's dream. I spent over 200 days in the outdoors last year doing any number of activities. This isn't because I don't work but because the outdoors is so accessible here, Biking is in town, Skiing is 25 minutes away, Climbing is in town plus Smith Rock is 30 minutes away, and great whitewater runs through town. If you enjoy outdoor sports, there are very few places comparable to Bend for accessibility, possibly Leavenworth, WA and Bozeman, MT.
2. The weather is very mild, we haven't really had a snow accumulation in Bend this year and it's January. The spring is short, summer hot, and fall is perfect. Winter is so much less harsh than winters in similar ski towns or even the front range in Colorado.
3. Housing was affordable for years but that is rapidly changing, I think this year was probably the largest shift in housing costs in Bend history as prices took a steep turn to the more expensive with the large influx of people who now have the ability to work remote. The shortage of housing is driving the increase in construction rates which has resulted in some very similar neighborhoods being developed but Bend is a very interesting city because it's booming so quickly and there aren't a lot of reasonable solutions other than building to meet needs and not shoot housing prices to the moon.
4. People are very friendly. There's this strange conflict between Bend natives and Californians which rarely comes up in actual day to day life. I think it has a lot to do with people who have lived here a long time being very frustrated that many of them are being priced out of their hometown and also some very poorly displayed attitudes on both sides of the fence. Overall though people are generally happy to chat or help out if you ever need it on the way to Bachelor or at a trailhead.
5. There's always something to do in Bend, even if outdoor sports aren't really your thing. Plenty of concerts, restaurants, bars, coffee shops, boutiques, dog parks, etc. For a town this size, we have a lot more than we should because we are a tourist town and generally have a population larger than the census report because there are so many people visiting.
6. Traffic, yes. Traffic Congestion, very rarely. I've lived in 8 cities now and this has less traffic than anywhere I've lived. If you're coming from Seattle, Portland, SF, LA you will think it's great... it's all about perspective and maybe not using arterial routes all the time.
7. Diversity. There's not a lot of it. You have to think about what brings people to Bend which is generally the outdoors. There are all kinds of problems that limit people from diverse backgrounds having access to outdoor sports. I really hope with what has happened this past year and a lot of outdoor retailers focusing on diversity, inclusion, and outreach that we will see a more diverse culture in Bend in the future but that will take some time. Overall, despite the lack of diversity, I really believe that Bend is a welcoming place for everyone.