This is a good thread. I like the real world examples. Multiple perspectives help give some actual insight to the current market.
I think the main reason many people complain that Portland prices are so high, is because they don't really understand what rents can be in the Portland market (with the right A class assets). High end units can rent for $3,000 per month, on a long term basis, to amazing tenants with 700+ credit scores. They rarely bother you and are no where near "one flat tire away from missed rent".
@Demjan Van Der Kach you have a ton of options in the Portland market. $500K with 20% down can get you a good long term investment in almost every market in Portland.
However, what I don't think has been pointed out is that your exit strategy really is a "flip" and I haven't heard anything about equity. Please excuse me if this comes out wrong, but this seems like pre crash activity to me. Leveraging a "rental" for 12 months (I'm assuming to avoid short term capital gains) and banking on appreciation, while buying retail is super risky.
Anything less than 6% appreciation will most likely result in a loss. Selling has costs which some people misunderstand. Those can/will offset an appreciating market, so you need to be buying with a discount to make this strategy successful. That's difficult to do in Portland without a lot of action and/or intimate knowledge of submarkets. Working with an agent on RMLS, without having a rehab budget in mind (to force appreciation), could bring even more risk to what could be a less than stellar acquisition.
I understand the 400K of leverage in the equation could result in a nice little return on your 100K with just a few points of net appreciation, it's just risky in my opinion. You can easily over pay, can easily see a slight shift in the market and concessions become a norm, you can see less than 6% appreciation, your tenant could trash the building, not pay rent, refuse to leave, etc..
If a 12 month resale truly is your exit strategy, there are probably a lot of lower risk ways to invest, that would result in better cash on cash return and less hassle.