Well, when learning evasion, they tell you your best buddy is lead time. It takes time for the folks following you to learn things. So yes, they know all this, but only after he's already done it. Did he take a bus a long distance away? Not if he's smart. Each change of direction makes their job harder.
So no five hour bus ride to Boston or three hour to Philly. Maybe you buy a ticket for there, but you get off at the first or second stop and move again in a different direction. Every hour you are out of custody increases the manpower required to cover everywhere you could be.
Prepaid cards to pay for stuff, set up drops with clothes to change. Get the clothes at any goodwill for cash. Doesn't take much. I'm sure they will get him, but it might be a while.