I've got similar concerns on a newish to me 1996 29.5. Has never had a dry bilge, the shaft packing, bad oring in AC raw water strainer and a hatch helped a LOT.
Now chasing what seems miniscule leakage, but the bilge pump will eventually run while I'm away. I'd estimate ~1 gallon per day, once the pump runs it's hard to say (no check valve) and it never goes below about 2 inches of clear water unattended.
Doing my sleuthing and found it coming from this stringer, ahead of the from keel bolt. Poking with a screwdriver and it was pretty soft, which let out a few cups of black water. FWIW this bit of fingerglass isn't part of the grid bonded to the hull - its a small tab with a hollow behind it. kind of suspect this hollow has been freezing solid in winter.
I know the boat has a history of leakage down the mast steel/ compression tube and also hatches.. But also some sandy groundings.... And i think i have a freshwater leak too. Ugh.
Any tips on inspecting the keel joint this winter haul? Or ruling out leakage from above, simply accumulating in the stringer? I should get a salinity tester.. I'm not sure I'm brave enough to taste this...