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My husband and I will be relocating to Bend in mid-July or August also. It is possible to find work, but I would suggest he has a job lined up before you make the move. It seems like most service jobs don't pay very well, and they are certainly not as plentiful in these harder economic times.
The westside is nice, but not the most affordable part of town. We are looking on the eastside, near the hospital, which is where my husband will be working. It is not as cute as the westside, but there are many established neighborhoods that are still somewhat close to downtown. It certainly would be possible to bike downtown from the eastside, which is what we are looking for. It seems to be family oriented too. I don't think you will have many problems with drugs in that part of town.
Has you husband looked for jobs yet? I would have him begin applying and getting his name out there. I really think that will be key to making in in Bend. Good luck on your move!
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