I think this is comparable to reefing. When you start thinking about it, that is when you should do it. Bring the
dinghy on deck when in doubt. If it is rough enough to capsize it, you are going to have a hell of a time righting it, and if your painter parts, going back and retrieving it.
I was cruising with a friend in 5 foot Lake Michigan seas and he was towing his
dinghy. The painter parted, and he felt retrieving the
dinghy was impractical so he let it go. The Coast Guard was very unhappy with that decision and threatened to charge him for the search they conducted when the cast off
dinghy was reported.
Bring it on board. Even in calm conditions it slows you down. Your boat will perform better and you won''t have to worry about it.