Does anyone have recommendations or suggestions for general contractors and architects with experience dealing with the city of Portland for a moderate size project like this? 

For others reading this in the same situation as me, there are a LOT of syndicators out there that also work with "sophisticated investors", which many of us with a moderate amount of real estate experience might qualify for.

Every time i post this the moderators delete it thinking I'm advertising.

@Karl Krentzel - since I am not a moderator, when I do an update to a post it will not let me create a hyperlink.

http://ngm.nationalgeographic.com/2013/05/longevity/hoffmann-photography#/05-irving-kahn-670.jpgI think I will be like this guy in that I will still do what I love but will just do it in moderation as I get older.

Let any one of the the moderators on here partner on a deal with you.

Several weeks ago, BP Moderators flagged my website URL which I (briefly) pointed to the consulting services tab on my RTPG website. 

MODERATOR:  DO NOT USE THIS THREAD TO PROMOTE YOUR OWN PODCAST.  

They are also fully insured (liability and workmen's comp).For a typical 2000 sf house, 3 color interior (trim, walls, ceiling) and a 3 color exterior (siding, trim, doors/shutters), plus moderate sheetrock prep/patching (total maybe two boards of patching and lots of prep) and moderate siding work (total maybe 10 boards of siding and lots of prep), they'd charge about $4500 (anywhere from $4000-5000).The additional benefit of working with them is that they sub out most of the rest of the work that doesn't require permits (demo, finish electrical, finish plumbing, carpet/vinyl, carpentry/doors, etc), so they manage about 70% of every rehab.

Especially for a moderator.