Well, they both always sell out within a couple weeks/months of sales opening. So yeah, people have done them and will be doing them, and on crappier bikes than whatever your worst fear is.

My only comment is that it's more fun to ride with friends than strangers and the route to PDX isn't difficult at all, so unless riding with 10,000 other people is immensely appealing to you, do it on your own or with buddies. It's just a bike ride, after all.