The downside is I currently make a hair over 65k a year and I can't afford to take much of a cut. 

But Portland market has been hot for awhile now and investors have been combing through that market's inventory for a decade.

Well, there's always Bitcoin :D.Seriously though - as much as I hate the hair-brained and pandering policies Seattle City Council and other similar governing bodies, I think we as landlords tend to blow the eviction thing out of proportion.

No evictions, makes good money.But.....she owns a hair salon....and I know how wild hairdresser types can be.....but that's a completely different story.

Then, you don't have to comb through your lease looking for some provision to hang your hat on in court to try and evict a paying tenant. 

Usually, if a broker is involved, the #1 would be offered for just a hair less than #2 (the price difference would be less than renovation cost).

I've been combing the MLS they seem to be exceedingly rare.  4) For FHA, I would need to be in there for a year before moving correct?  

Once you've done the reasearch, presented and had shot down several deals by us "gray hairs" and have truly stumbled onto a "unpolished diamond" you'll know it.At that point you'll have the money, the skills and the aptitude to "walk the talk".

They want transactions with the least amount of "hair" on the deals as possible.

Another issue will be showing that your contract is in compliance with new laws according to when it was made, if it is not in compliance then it may not be marketable at all or may require a shaving, not just a hair cut.