It has improved a lot as their data and algorithms have both improved. 

For one, some of the things you describe are already happening, but on the lending side of the equation (see FHA & some conventional 90 day anti-flipping rule, or 180 day 2nd appraisal & proof of improvements rules some lenders have, as well as 20% over purchase price restrictions).  

Hi BP,What platforms, businesses, methods, have you been using to improve your investing? 

@Russell Brazil so you do not think that place will improve in a few years, especially with a developer purchase of Iverson mall?

I think I'd try hard to break even or get a little positive cash, and then find something closer to your new location where you can improve your net.

Dani Z mentioned it but other thing to keep in mind with Portland as they MAY require frontage improvements to do the land division if there are no sidewalks.  

Maybe he is a lot busier these days (market has improved) it may not be worth it to him now.Look at it from his side, however seek out someone who can accomplish what you need with full cooperation and understanding of your goals.

If the property can be improved enough, it just comes off the top end - IE instead of clearing 20k lets say you might clear 15k because of 5k in additional bank costs. 

If I could buy the house I would drastically improve its value and this would help the neighbors current situation as well. 

Sounds like you need to sell one of them so you can afford to maintain and improve the other 2.