Well, I’ve been out of the Horse Show scene in Bend since I was a teenager and left for college, so most of my ‘help’ will have to do with climate, typical management, etc.
I rode back when the first rated show was the Michelob Classic, at Stevenson’s Polo Barn. (That one is now the giant two week summer High Desert Classics I and II, at a different location.) Local series were good, and fun, the Stirrup Cup ran a series and in the fall we all went to Liddy Hilbruner’s place in Tumalo for the Tumalo Hunter Trials- real galloping course with water hazard and all.
Anyway…
Central Oregon has some dandy farriers- more than just one or two top guys to choose from, a ‘normal’ set of shoes with no pads, trailers, wedges, etc will cost around $100, from a Very Good Farrier.
Very Good Vets are also around. Some have good clinics, some are mostly ambulatory. A facility was built in, I don’t know exactly, but around 1995 or so, that will accommodate emergency colic surgery, neonatal foal problems, and such. It used to be a 2+ hour haul ‘over the mountains’ to the vet school at OSU in Corvallis if you had a seriously bad problem.
There are a couple of great horse chiropractors around, as well.
Hauling over the mountain pass is not a big deal in the summer. It can be a nightmare in the winter. For most of the late spring, summer and early fall shows, you’d be fine. If you’re thinking 4 or 5 rated shows a year, you’d have no problem at all. But if you’re going after year-end awards and need points, the Valley (Portland/Eugene) might be a better choice.
Others might answer better, but I think there are plenty of schooling shows to go to, with real jumps and proper distances and judges that can reasonably judge.
Horse management:
Bend is in a high desert climate. If the ground is irrigated, it grows rocket fuel. (If it isn’t irrigated, it grows dirt, rocks, sagebrush, and junipers.) If you have a horse prone to insulin resistance or founder, you’re going to have to limit turnout, use a grazing muzzle, and have a savvy barn manager.
The Willamette Valley is wet. It grows ‘washy’ grass, lots of green and lots of volume but not a lot of nutrition. The local hay is usually not nearly as palatable as Eastern Oregon hay, but you are not as likely to founder an air fern on green turnout.
The rainy climate on the west side of the Cascades will mean you’re indoors all winter long, and turnout might not exist. It gets muddy. REALLY muddy.
On the east side, it gets a lot colder and there will be snow and frozen ground to deal with, so December and January will be indoors. But there’s only one year in ‘recent’ memory (1992-93) when it snowed in November and stayed white until March, so you’ll be able to ride outside, on trails, and such some during the winter according to the weather.
I rarely want to ride in December or January, those are good times to pull shoes, let the horse get fuzzy and turn 'em out. But the cold weather can come up as late as June…it will be warm and green and lovely (except for the mud) in the Valley in March, and it will be cold, gray and windy in March in Bend.
I’d second the idea of visiting barns in the winter, to see what’s up.
Anyway, I wish you the best with your decision.