It's a business - acquiring/building, managing, and growing a business. 

Quote from @Kolby Knickerbocker:  Have you considered building here in Central Oregon or an STR here? 

However, building a relationship on a lack of disclosure or a lie isn't probably the best idea, let alone the ethics of the matter.Hope this helps.

You will also likely be paying more than more experienced investors as you build your team and knowledge.

First off, I really like how you’re thinking beyond just the renovation.. you’re creating a tailored investor strategy that builds excitement around upscale features.

You'll get a feel for the age of the neighborhoods, the vitality of the commercial buildings, the ease of location, the closeness to jobs.The markets you're describing are more linear, and usually have lower capital appreciation.

While your condo snowball strategy builds equity, modest cash flow and HOA fees may limit returns.

What Brand and color paint would you guys suggest?

That will allow you to build the additional legal space further amplifying the value of the proprety (more HELOC money). 

@Ketch BaysStarting small in a cash-flowing market is a smart way to gain experience and build confidence without overextending yourself financially.