Joe Berk has organized rides for the TT250, similar to how he has organized rides for the RX3. In other words, gear it for cruising with a lower 40 tooth vs. the 47 tooth you want, as Megadan pointed out, and prep it a bit (i.e. fresh oil change, check the chain, spark plug and consider carrying an extra chain, spark plug, and perhaps a CDI--maybe a little overdramatic? Or just good proactive measures?) and you should have little to nothing to worry about.
