Re: A little freaked about a big roadtrip with toddler. Advice please!
We regularly take trips of about 6-10 hours, and have since DS was born. DS is 4 and DD, almost 17 months. She is very active, but is generally a good passenger. We've driven during the day and at night (leaving around the kids' bedtime). For me (the driver), it's far easier to drive at night: less traffic, the kids will sleep at least part of the trip, as will my DW. During our daylight travel, we pack special treats (special snacks, small, quiet toys, a ball or frisbee for stops). We stop frequently and make sure to get out and run around for a while before getting back into the car. We don't have a DVD player in the car, and have no plans to buy one.
I'd take a practice trip of 3-4 hours roundtrip beforehand, if possible, to get a sense of how your DS might do, esp. if you haven't driven a longer distance with him yet.
If you're willing to drive all night, you could easily do a 14 hour drive starting at dinner time and getting in around breakfast time, especially if you have 2 drivers to trade off driving/sleeping shifts. (that's probably what I would do.)
SAHD to J 12.27.05, M 12.27.08, and A 2.15.11.