I have been analyzing this deal to death and I feel as though I need a fresh outlook to provide suggestions.

With the limited info that you provided, I personally would keep it in my portfolio as long as the unit is cash flow positive and the outlook for the location and overall rental market is positive.  

It is great to hear about the long term outlook on deals and investing.

I've love to hear any opinions about the long-term (15-20 year) real estate appreciation prospects for Portland, OR.  I'm not really an investor, but do own one single-family house in a great inner east-side neighborh...

You will have to cut around the edges to get them out. Look

Hopefully, he will have a better outlook on those properties when they are fully renovated, but we can only hope.Secondly, maybe breaking the comps by 10k in my area for the price range of houses I am working with a is a bit too much.

Some lenders advertise 10%, but with all of their fixed fees and whatnot, at a lower price point (like $50k) it comes out looking like 20%.

When I first started out looking for deals for other investors and got into wholesaling, I had to try a few different methods. 

Hey @John ParshallAs others have mentioned, the current legislative landscape leaves the outlook on the viability of STR investments in SD a bit up in the air.However, as @Dan Heuschele stated, ensuring that the property is viable as a long-term rental will drastically reduce the risk associated with that uncertainty. 

More details needed to offer advice: Monthly Mortgage Payment, outlook for speed of getting it rented, type of neighborhood (A,B,C,D)., what Cash Flow do you anticipate, etc.