Actually, both ARE quicker than the above suggested route. I've been all the routes mentioned so far and while the one Kyle suggests is a bit more scenic, it WILL add at least 6 hours to the trip. Rt. 2 is two lane road that slows down and/or has stops in every little town/village it passes through. Nice drive? yes, but slooow.
Getting to 90 from Portland involves either a bit of "backtracking" or a little out of the way, but it is a very nice route and one I like to drive. Not quite so steep as sections of 70 or 80 as well. Personally I would go the 84 to 80 route and not worry too much about it. I've driven several different Penske trucks cross-country and all of them had adequate power, not abundant power, but adequate. The major problem with 80 is the Chicago/Gary section. Busy with traffic and usually construction this time of year. If you do choose either 70 or 80 when you get into MI don't travel along the bottom of the state on 94, that road will beat you to death in a truck. If coming in on 80, it turns into 80/94 on the South side of Chicago, stick to 94 when it splits again (saving toll charges and a little time on 80) and take 94 into Michigan. At about mile marker 34 or so in Michigan, take 196/US-31 North and follow 196 all the way into Grand Rapids then take 96 toward Lansing. Just outside of Lansing take 69 toward Flint. At Flint take 75 North and then just outside of bay City change over to US10 toward Midland.
Without the truck I would say take 90 across then head over to US-10 so you could take the ferry across the lake to Michigan and then straight down US-10 to Midland, but it would be kind of spendy to take the truck across I believe, and you would have to take the
USS Badger because
Lake Express doesn't do bigger trucks AFAIK. This looks like it is the last year the Badger will be coal fired (last of it's kind in the World right now) because they are talking about converting it to oil fired during this winters lay-up due to EPA rules. It would make kind of a cool side note to the trip, and you would get to see a 60 mile wide stretch of Lake Michigan while taking a 4 hour rest from driving.