Recommendations for first-time visitors in January?

My partner and I are going to be in Portland for four days in mid-January. We're in our mid-30s & haven't been before (we've only done Seattle) so we're trying to get a feel for what the city/greater Metro is like in the winter and what we should/shouldn't miss.

We're toying with the idea of moving here next year. Currently live in Florida (I'm originally from upstate NY, my partner's a lifelong Floridian). Part of this trip is just seeing how Portland feels day-to-day, not just the tourist stuff.

Side note- we're coming in January because I think it's important to visit a place, especially somewhere sometimes thinking about moving, In the off-season (Florida in August for example).

I really appreciate any advice and recommendations. Good or bad.