Hi Frank,
I'm a real estate agent and investor here in OR. I live on the west side in McMinnville. I'm centered here for now but think I'll be moving into Portland within the year. I invest in McMinnville because we renovate older homes with character and do vacation rentals. Our business is focused on the wine industry that runs up and down the Willamette Valley. We've focused and created a little niche for ourselves.
I mention this only to say, it depends what you are wanting to do with the properties as to whether Bend is a good area or not. Knowing what I do about the tourism over there, I think you might have better luck at vacation rentals. I have found that because of our relatively high purchase prices in OR, it is hard to get the same cap rates as other areas. And yet, rents are not that much higher when you get out of Portland metro. The other great thing about vacation rentals is that it takes rent control and tenant laws out of the equation as those laws don't apply to vacation rental properties.
To be sure, there are plenty of other laws that do effect you as an investor if you go this route.
If you'd be interested in a conversation, I'd be happy to tell you more about what we do and why. Depending on your interest, we could always talk about working together somehow too.
Best of luck! I've only been in Real Estate investing and sales for about 3 years now and it has totally changed my life. It's a wild, fun ride!
Cheers,
Tim