1. The coast of Oregon tends to be wetter/windier but more consistent temperatures. The coast range gets some snow but not an awful lot. The cascade range gets significantly more snow. East of the cascades Oregon stops being wet and starts being dry. I'd suggest looking at precipitation maps and temperature maps to get an idea of the ranges.
2. Fun depends on what you want to do. Hunting and fishing would put you in a very different location from eating at nice restaurants and being into boating.
3. Oregon is pretty open carry friendly in my opinion. It isn't Arizona, but even the liberal places tend to not really care. The downside of Oregon is that there isn't state preemption for unlicensed open carry, but none of that matters if you get a CHL. In Oregon you can carry pretty much anywhere other than secure areas of airports, jails, courts (I think), post offices, and federal buildings.
4. I have no idea what the job market is for customer service/sales. There's lots of industry sprinkled throughout the state, but obviously Portland is going to have the most job openings.
5. Not too familiar with the rest of the state, but I know Corvallis has a year round farmers market. I'd be surprised if Portland didn't or other larger cities.
Downsides to Oregon are the income tax which Washington lacks, but in Oregon you can own machine guns. But then in Washington you can smoke marijuana for recreational purposes.
I'd recommend taking a vacation out here and driving through the areas you think might work.