The east side of the Cascades is definitely drier. It's High Desert and the weather typically comes in from the ocean and first hits the 3000 foot high Coast Range which takes a lot of the moisture out of the clouds. Then whatever weather is left drizzles the rest of the rain into the Willamette Valley before it runs into the Casacdes which range from 5000 to 11,000 feet high in Oregon. That leaves little rain once the weather moves over the Cascades.
However, this means like 300+ days of sun each year in that area. It also means less temperate weather so you will get hotter in the summer and colder and more snowy in the winter than the west side of the Cascades.
Bend is a great area. Used to be big timber industry but when that went belly up, it became more of a getaway destination. It has arguably the best views of the mountains in Oregon with 6 or 7 big volcanoes right there. You've got the best skiing in Oregon at Bachelor, tons of mountain biking, golfing, rafting and of course Smith Rock. Prineville is a bit east and is more "rural" but is great if you want a small town feel in the eastern desert. Redmond looks to want to become another Bend soon in my opinion. Not a bad place but personally, I like Bend better. Seems to be a bit more culture in Bend to me (sorry any Redmondites who may be reading this), restaurants, concerts, medical care, shopping, housing, etc.
If I didn't live in Portland, I'd want to live in Bend. But you should take a trip to those areas and check them out for yourself. What is one man's haven could be another's idea of the end of the earth.