I think you will like Bend. I lived in that area a couple different occasions. I took two semesters of art at COCC. I don't know how much has changed in 15 yrs, but parking was at a premium. Plenty of walking up and down the hill...you will get some exercise between classes, lol.
Rent wasn't cheap either especially on the west side where it was a little trendier.
At that time I leased a good chunk of ground so I could have my horses where I lived and exchanged rent for changing handline in the alfalfa fields. I worked early mornings feeding, cleaning stalls and turning horses out at a dressage/jumper barn down the road, Orion Farms, before class. Back then board was over $500 a month..eek! LOL. If I remember right Joren Traveller was the dressage trainer there at the time. Pretty place, and close to trails, I think it backed up to National Forest. It may not be there anymore.
I don't think there is any shortage of barns to go to, but again this was several years ago :)
I DON'T LEAD 'EM AND FEED 'EM, I RIDE 'EM AND SLIDE 'EM.