Okay all you experienced old boat modders.

I'm putting in a rode locker with a shelf and drains above the waterline as suggested by Annie and David Tyler.

There is an 8 inch vertical rib running from the stem back aft past the locker bulkhead, making it nearly impossible to sand or grind away the paint in that tight, pinched area.  The photo below doesn't really convey how cramped it is.  I was able to clean and scrub it well enough with a thin and long handled wire brush, and I can probably lay in fillets and glass with some finger extenders.

This area is going to be chronically wet, what with the drains and all. How much trouble am I asking for by glassing over this old paint?  Should I extend the fillets, or some 10 oz cloth, up the sides of the hull for an extra foot to keep the old paint / new glass seam above most of the wet?