The layout leaves much to be desired.

Then you'll really know if they're doing their job, after all you've teed up the applicants.It might be passive aggressive, but it will get you the results you desire! 

It's in Ashland, Oregon (a very desirable community) in a very desirable neighborhood.

And no, I have no desire to work commission.

There are 2 main things I would look for in a co-op and in retrospect maybe have even bought a smaller place in a less desirable area to gain these two things:1.

The other option would be to increase rents, but this is less desirable because your rents may be higher than other units around you.  

- do I have the time / desire to manage a remodel (of new house) while managing tenants (in current house)?

What can help make your decision easier is to list out all the pros and cons on flashcards for each purchase option (desirable duplex vs other investment) and to order each in terms of importance. 

(I feel this is the least desirable/most expensive way, but may be easier to find properties)

I can't answer your first question without doing an in depth market analysis.Your second question, you take the sold comps and subtract your budget for rehab and buy, and if the result is at least equal to your desired budget, that's a profitable property.