What I'm trying to do now is identifying the markets I want to go into as Portland real estate prices are too high for my budget. 

It's hard to determine what makes you tick before you identify where to insert the batteries ;)

I 100% agree with @Jon Holdman This problem should have been identified and solved prior to purchase of the property... or should i say properties.

I have identified a few "ugly house" duplexes in a good market near me that are not yet on the MLS.

So in this case in escrow withholding 50% capital gain tax for my sister, my 50% tax defer to 1031 exchange identified property in 45 days from close of escrow.

As you will read in many forum post, many investors may have some combination of or even none of these items you identified as hurdles.  

So I am asking for help with two things:a)Feedback/experience in this nicheb)Can you help me identify resources to learn more about this niche?

I like the idea of getting at least 3 bids as well until I have gained enough data to know what I should be spending and until I can identify contractors that I can trust and work with well. 

Thanks for sharing your list of criteria values and identifying your investment vehicles towards your objectives and freedom.

Identifying tells, understanding statistics, representing strength or weakness, considering your position/table image and maintaining discipline are all more important.