I have to echo voyaging's response to you saying you don't get responses. You asked one question about getting to wine country and coast from Portland and received a prompt reply. I was going to respond also to be sure you meant the Willamette Valley wine country near Portland and not the southern Willamette Valley, Umpqua or southern Oregon wine districts. But I figured the answer you got was what you wanted...so I left it alone.
However, not I WILL ask some questions that you need to answer to get useful information from us. Are you doing a loop back to SF? Are the 5 days all travel days or do we need to subtract time you might be spending in SF?
How many hours a day are you comfortable driving? You say you are coming from SF, but your headline says south Oregon to north Oregon (excluding the time from SF to Oregon?). If you go up 101 through the redwoods, it'll take you about 7 hours to Crescent City. You can then go up the coast as far as Newport or Lincoln City before cutting over to the I-5 to Portland. If you have to return to SF, you'll probably only have time to shoot straight down I-5.
You can take the #18 from Lincoln City thru McMinnville and the wine country on your way to Portland. You would not have time for a tour of the wine country, though, unless you cut out something else on your itinerary. If this is a one-way trip, it'll give you at least one extra day.
Now...look things over and give us your sightseeing priorities and we'll help you further. Decide where you want to spend two nights and we can adjust your itinerary accordingly.
But, please, don't say no one answers your questions.