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I have also been considering both Portland and Louisville as places to move - either would depend on a job offer, but I have looked at both. I have spent more time in Portland and been closer to getting a job offer there, so here are 2 comments I would have about Portland:
1. Portland is definitely more expensive than Louisville, especially if you want to live in a school district that is considered better. Places like Beaverton, Tualitin and Tigard are nice, but more expensive than other areas that aren't rated as highly for schools - Lake Oswego is the upper end of all of those. The same is true of areas within the city limits that have good schools as well. There are a few really nice older neighborhoods within the Portland school district, but those neighborhoods are expensive to live in (relative to other areas in Portland).
I don't think this pattern is different from what you will find in Louisville or any other mid to large sized city, but the dollar numbers of the costs are higher in Portland.
2. One thing to be aware of in Portland is that it is one of the worst areas in the country for meth use. That is not to say it is a problem everywhere in Portland, just that you need to be aware of it and choose where to live accordingly - The nicer areas will probably have less of a problem with this, but you will pay more to live there.
All that being said, I personally would choose Portland over Lousiville, but my reasoning includes proximity to family which bears no reflection on the cities themselves, just a fact of my my personal situation.
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