Just wondering if there were folks on here who've done a road trip across the longest highway in the states. I'm planning on doing it with a couple buddies sometime next Spring but I'm not sure if that would be a good time due to snow/wintery conditions. 

We'll probably do it in 2-3 spells, making 'pit stops' in various parts(MN, Chitown, et al) before we reach our final destination, Boston. 

Any tips/suggestions will be highly appreciated. 

 I hv driven I-10,40,5,15  many times, but never been to far northen part so dont know about ice.  For one driver dont go more the 500 miles a day if u going for fun or dont go more then 800 miles a day anyway if you wanna reach safe. Stop and get refreshed every couple of hours. Keep extra tyre, some food and water for emergency. For rest of stuffs: have cash or credit card, you can buy almost everythig on the way.

Just Do it.
http://www.interstate-guide.com/i-090.html

Oh myann. Thats something i really wanna do.
I gotta save my holidays so that I can go to NEPAL around December 2013. Lets See.

If you really have some extra time. YOu can also go for CA - Voncouver and then start I-90 since you are local to CA anyways.

I visit Portland all the time (just moved from there) and it's not really that fun. Always wanted to go to Vancouver though but I still haven't managed to do it. 

What will be your starting point ?  I mean East to West or west to east?

Do you like Camping? Then you guys can camp. 

We're planning to start from Seattle and end in Boston. 

 Good luck, riddle bro.

 Just saw your edited post, Magorkhe. Camping is a great suggestion. Not sure if it'll be applicable during Spring though. 

NY has this rules:

• Except in an emergency or between December 15th and April 30th, camping is prohibited above an elevation of 4,000 feet in the Adirondacks.
• Except in an emergency or between December 21st and March 21st, camping is prohibited above an elevation of 3,500 feet in the Catskills.
• At all times, only emergency fires are permitted above 4,000 feet in the Adirondacks and 3,500 feet in the Catskills.

Check for each State you are willing to camp.

Camping will be real fun, make sure its not bear prone area.

 Can't tell if you guys are mocking me or giving genuine inputs. The entire Northern region across the mighty nation will be blanketed by snow during Spring and you lot are suggesting that we camped? 

Honestly; I did not considered the season while suggesting.

 Thx for your input, nevertheless.