You might look in the Powell Butte area of Southeast Portland. Or Sandy, in rural Clackamas County, Oregon CIty, Mollalla, Estacada, or Canby corridors. All offer real bargains compared to the city.
Possible site in Wine Country communities too, west of Portland...like Newberg or Sherwood, but traffic can be an issue. Beautiful country, here, so if you enjoy that aspect of driving, parhaps choose a country road commute, rather than a freeway? Can you work part-time from a home office?
We have lots of excellent Brokers here who can help you find a place that fits your whole list.
Often a larger property will offer Rental or Lease possibilities to allow you to make a higher offer.
(I'm pretty familiar with the market right now and have seen some great ones recently. Can act as a Finder for you if you, and do research on the properties if prefer to look without a Broker - until you are ready to negotiate & write your Offers. Zillow.com can help you assess some info from Public Records, as can www.PortlandMaps.com Trulia's map search function is a good place to start, using the town names I suggested above. Have fun with it - and Good Luck!