YES, I've done it!
The maststep on my 1979 DS II actually needed to be totally rebuilt not long after I bought her in 1996, and again in 2007 to correct my mistakes from the first time <GRIN!>
The problem is that there is no real easy access to the underside of the cuddy floor. I originally cut an access panel just aft of and to port of the maststep, were I to do it again, I might take a router or Dremel Tool and cut out the cuddy deck around the maststep to access the rotten plywood, then replace the wood (being sure to seal it well with epoxy) and then glass over the area. Part of the second rebuild that I did was to relocate the plastic pipe under the cuddy floor that is supposed to support the maststep, mine was located about 4" or so Forward of the maststep! The cuddy floor had cracked and been "repaired" by the former owner, but he wasn't exactly a fiberglass repair expert! Let me tell you, it was quite a BANG when his repair let go! The mast suddenly dropped an inch or two, creating slack in the standing rigging...... I made it back to the mooring fine, but you can bet that I made temporary repairs right away!
Anyway, I know have a far stronger maststep than the original, all the plywood under hte cuddy floor is new as well as I added a 1/4" aluminum plate (about 1.5 ft sq) on top of the cuddy floor which spreads out the pressure of the maststep and also provides more secure mounts for the CB control blocks. My mastep is actually now bolted through the new plywood using blind nuts in the new plywood, but you could still use stainless steel wood screws (or sheet metal screws) as long as you bed the screws and maststep in sealant.
I have included 4 pictures below, the first 3 are of my boat, the 4th is of a fellow Day Sailer owner's 1974 DS II. His pic shows the basic view of the original construction. I wish now that I'd taken pics of my boat before I made the first repairs! Like yours, mine had rotted out (water in the bilge was big problem, due to a leaking repair in the bottom of the boat....did I mention about the time the boat was hit by lightning 11 years before I bought her? Well, that's another story for another time!)