For those living in Oregon, please let me know which is the best way for my trip!

My former supervisor is getting on the Sunday of Memorial Day weekend. My coworkers and I are planning to fly into Portland on that Saturday from San Francisco. Their wedding is in Salem and upon checking it’s slightly less than 50 miles from Portland. We are getting a rental car and our plan is to explore Portland on Saturday then drive down to Salem at night and stay there. Since her wedding isn’t till 4:30 pm we are thinking of exploring Salem before it. Our plan then is to drive back to Portland Sunday where they’ll catch their flight home while I remain in Portland for another day. Amtrack can take me back to Portland from Salem so I don’t necessarily need to ride back with my coworkers. My question though is would it be better if we stayed in Portland and drive to the wedding next day or should we just stay in Salem? I’m more worried about them making their flight as it’s still almost an hour drive back but I don’t want time they’re flying back yet.

What would you guys recommend that we do? Thanks!