This year it was about $8000 for a west to east container. We ended up not doing it and tripple stacking a trailer and chartering one boat and another drove themself. It's a long drive 4 to 5 days unless you drive 24/7.
What were the total costs of this option (gas, tolls, hotels, meals for the drivers)? Did you save ANY money? Sounds like costs of 2 tow vehicles, plus the cost of 1 charter boat to be included in the calculation.
I've looked at the costs of a cross-country jaunt. For my RV (est. 7 mpg), the gas alone is something like $3500, no idea about tolls. Of course, you can drive straight through (rotate drivers sleeping in back), avoid hotels and eat out of the fridge (cheaper than stopping at restaurants or fast food). But, you're limited by how many boats will fit on the trailer (and won't stress the tow vehicle), which will increase the cost per team.
Speaking of which... there's always the possibility of unplanned repairs mid-route. I've double-stacked from New England to FL 3 times. Each trip required the tow vehicle (3 different ones) to be repaired just to get home. Fortunately, one time, the vehicle was driveable enough to make it to the regatta, and the other two times the breakdown happened on the return trip, so we didn't actually miss any of the regattas. 2 of them required transmission work, which meant finding an uplanned way home from mid-trip, then back to retrieve the vehicle and boats after the repairs were complete. Good times... (And no, we don't use that trailer anymore, it killed another vehicle on a trip to Madcatter, so it's officially cursed.)
So, if a container will hold 8 boats (or if you have 5 teams to share it), would it be cheaper anyway?
(I know, there's the hidden "cost" of losing your boat to shipping for a month or more with getting it shipped at the height of regatta season.)
Mike