Any contractor that has an issue with this is a red flag anyway.

I know I can do better than 2.5%, so it's time for me to sell my "green house" and 1031 into a "red hotel."

If there are some red flags, don’t hesitate to request additional deposit or a co-signer.

I ran some really quick numbers and I don't think you'll be making a ton of cash flow on this property with a $1,400 mortgage payment, and would be careful with a HELOC, as that might run you into the red. 

as screwed up as Portland is politically.. the RE market like many areas is quite robust to red hot.. 

Regarding this deal in particular, it sounds like the exit strategies are limited, which is a huge red flag.

You've sought out an agent to work off market deals for you (ethical red flag and possibly not legal for an agent to do according to NAR), then they BROUGHT YOU A GREAT DEAL, and now you're concerned that they might have a motive other than your benefit?

Also, on a complete side note, is it a red flag if a property in the north-east doesn't have a heating system for a period of time in the winter? 

The older gentleman is a doctor and his credit and background check come back great no red flags there.

100% agree with @John Warren make sure you aren't in a war zone and those prices for a newer built building are a red flag.