Hi Greg -
In the Eastern US or Bahamas I can't imagine a situation where you'd need more than ~100' of 5/16 HT chain for your boat, backed by another 150+' of rope rode. Anything else is excessive weight, IMHO. You'd have to decide whether that's worth the cost of changing the gypsy. I have a spare (moderately used) 5/16" HT gypsy from a Lewmar Ocean 1 series windlass, so PM me if interested. I don't know how specialized (fit) those are.
In the Eastern US or Bahamas I can't imagine a situation where you'd need more than ~100' of 5/16 HT chain for your boat, backed by another 150+' of rope rode. Anything else is excessive weight, IMHO. You'd have to decide whether that's worth the cost of changing the gypsy. I have a spare (moderately used) 5/16" HT gypsy from a Lewmar Ocean 1 series windlass, so PM me if interested. I don't know how specialized (fit) those are.