If it was just a couple of hours on country roads then I’d consider it to be honest. What worries me is getting the bike from somewhere in the Chicago burbs to those country roads. I have passed the MSF but have not ridden in traffic. Chicago traffic would be more of a baptism of fire than I’m looking for.
I will do some calling locally to see whats available but craigslist has no 250 cc bikes in my area and my local Honda dealer has no 250cc bikes of any description until the 2009’s start arriving.