Would I get in NOW.... no, especially if money was the issue - go to
www.everytruckjob.com and run a search for "student / recent grad" and your state, or a state near you, and see who is hiring first... I wish I could say this to anyone considering truck driving school; "...don't listen to the hype, first see IF you could get hired and then shell out the money..." I could tell your horror story after horror story of people with felonies or misdemenors that were told "...you'll make 50k a year..." paid the money and now find out NO ONE is trucking would ever hire them...
So like anything, research first, call around, and be frank as "if" you went to school if they would hire you when you graduated. Tell them about your legal past, and see if the type of school you'd need to go to might help your chances.
We have about another 14 months of downturn left, but on the bright side trucking is the FIRST thing to improve in an economy before anything else.