Sanding, Sanding, effing Sanding

Hi all,

I realize this topic has probably been covered a gazillion times in the forum, but I find the search feature a little lacking.  Sometimes I get better results from the builders forum by putting my search directly into Google.

But alas, I stray from the topic.
I am prepping my Annapolis Wherry for painting and varnish and resigned to the hours of sanding I am facing.  I understand I am trying to achieve a consistent uniform cloudy sheen on the epoxied surfaces.  However the challenge I lose more often than not is to do this without sanding into the wood or the glass.  And in the case of wood, then having to re-epoxy.  

I can usually get to the point of having most of the surface consistent with a few pin-prick type of depressions (picture 1).  But then going a little further puts me into the wood (picture 2).  
I also have a particularly hard time with the fillets, as mine are irregular and contain nooks and crannies which are hard to get the sanding pad into.  Using the scotch brite pads helps a little but not much (picture 3).
Quesitons:
1) does leaving a few pin-pricks cause a problem (say less than 1% of the surface area)

2) If I can eliminate the "glossy/shiny" spots, but it is not quite a uniform cloudy sheen, is that sufficient?

3) Any suggestions for handling fillets?