Paul. I have found that Deans battery connectors are more reliable than the usual ones, and to be honest I have had no trouble with ordinary wire connectors that you would get at Maplins.
HOWEVER, the 3 or 4mm gold plated types would be the ones to go for ultimately, any good shop/supplier will have them. These need to be soldered and then a little heat-shrink sleeve fitted, the ultimate in reliability.
Lunchboxes: For sarnies only (my opinion), and as per Malcolms post, arranging that the gear is off the bottom should be more than adequate. As he says. assume some will get in (there is always a dribble) and simply lift the gear a bit. If any more than a dribble gets in, there is something desperately wrong and the boat needs to be hoofed out the water, or indeed, not put in in the first place.
Ashley