Nice boat there!
Boot stripe problem might be fixed by stationing someone of equal weight in the bow.

The little ramps in the scuppers have caused puddling in the deck aft of the thru-deck scupper next to the coamings.
If you keep the edge sharp there where water exits (when you take the wedges out) it is less likely to dribble down the transom. It's boats that sit around collecting dust that have a stain problem.