I think you'll do great outdoors in Bend. I'm a bit north of you, but I run into a LOT of rain issues starting around the end of September, early October. Luckily in Bend you get significantly more sun than us growers in the North of the state. Up around where I'm living anything going past the end of September starts to make me nervous as PM and budrot becomes a serious issue. After late September the weather becomes a roll of the dice. You can see my outdoor grow from last season in my signature.
I'd take shortening days and cold into consideration when making strain choices. Unless you're growing in a climate controlled greenhouse, I wouldn't risk going past Mid October outdoors, so I'd be looking at 8-9 week strains primarily. I know a few growers out your way that have run 10-11 weekers, but they were utilizing greenhouses to extend their growing season.
I haven't had to deal with mold on any outdoor plants in the Willamette valley yet. Its bortytis spread by those green caterpillars that will ruin bud
Experience: 2 outdoor seasons
Location: Oregon coast range
Advice: Pick hardy strains. Expect to lose some to mold/rot.
I have an assortment of Bodhi, KC Brains, and Hybrids From Hell genetics. I picked them because those guys breed outdoors, and the strains I picked were recommended for such.
I've let some sativa dominant stuff (KC) go to second week of November, and it had VERY little mold/rot loss...certainly much less than indica stuff chopped in late September. The November stuff went through some HEAVY wind and rain, but good genes and open bud structure seemed to shrug it off.