Vantaggi
The people are great. My immediate manager is one of the best I've ever had. There are a lot of people who have been here 10, 15, or even 20 years, which speaks to how good it is. We're given the time to do a good job and very rarely are we in emergency mode where we need to work 50 hour weeks, on weekends, etc. Good work-life balance. Just moved to a brand new office in downtown Portland that is pretty nice and is in a great location near transit, etc.
Svantaggi
There is a lot of technical debt to deal with, but that's slowly being worked through. It's to be expected at a 30 year old company. The benefits are terrible although the pay is inline with the market. Health insurance is incredibly expensive, 401K match is stingy. There is some resistance to using newer technologies although that is getting better. The release process is kind of a mess with an adversarial feeling between IT and development.