living space

Today I've been looking for places to live in Portland. It's such a big task! We have never looked for homes together before, because for the last two years we have lived in Fuller housing. I'm learning about loans and how so many different things like type of homes, locations, amenities, etc influence price. How could one ever know what a good price for the value is? At least, as an amateur, I'm having a really hard time figuring it out. Of course, there is the percentage of value versus other comparable sales in the area, but what about home versus condo, condo versus apartment? One site says that it's best to rent right now because the cost of housing is still falling right now. But if it's falling, don't I want to buy it now instead of when it is soaring upward? Makes sense to me. I guess we will learn a lot when we go to Portland and view several of properties. Right now I'm feeling overwhelmed, but ready to move out of our stinky apartment.