I live in Bend, OR. Have for 20 years. If I were in your shoes and this is the God honest truth...
Option 1: You are retired and have over 2 million in savings. YES!!! Move to Bend.
Option 2: You are still working/going to start a business and do not yet have 2 million in savings. NO!!! Stay the hell away from Bend unless you want to live paycheck to paycheck for the rest of your life.
Reason? There are NO good paying jobs (unless you are in medical to take care of all our old farts) and any good job is already taken by mass competition/Dr.'s flipping burgers just to live here.
Coming from a successful business owner of 20 years who can have my pick of college grads for minimum wage 365 days a year.
Is Bend what it's all made up to be? Not any more. It's getting big really fast and doesn't look to slow down. Its doubled in population every decade since the 90's. It's on the verge of a big city not a small town feel. Still love living here and this is where I have my company based out of and if you have a job with long term reliability then by all means Bend is a great place to live.
PS. our population is currently 80% Californian transplants. So it's Bend, CA NOT Bend, OR.
PSS. DON'T be an idiot and buy a house in Bend right now. The market is super over inflated. Remember what you learned in kindergarten... buy low, sell high. I swear people do the reverse with homes. Ex: my neighbor just sold his house for $649,900 a month ago. Exact same floor plan as me. I bought my home in 2002 for $88,500. 2007 price was high, 2008 you could get a home for free in bend as half the town was abandoned. 2016 prices are high again... 2017 will half our town be Detroit again?!? I don't know.
I'm rambling. Good luck to you where ever you end up! But there are much better places to live then Bend, OR if you are still working or are looking at buying a home.