When you say "live well" are you referring to the front fish boxes or the bait well? I assume you mean the fish boxes because the bait well has a rubber stopper used to keep water in or out.
On my 170CC the drain holes were not completely round so I had to run a drill through them to "true the hole up". After that I turned the plug handle to tighten them up and haven't had a problem. If the hole is too large for your plugs then you may want to enlarge them and install a garboard drain plug like this one from Boaters World:
http://www.boatersworld.com/product/326790482.htm
Just a thought. I hope this helps.