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My biggest problem is likely to be redundancy in labeling. big fish hole, big fish hole A, big fish hole B

One thing to watch out for, depending on how your software works.  In Garmin's Mapsource software, you can give waypoints with maybe 14 characters in the name.
But the maximum length of a waypoint name in my old Garm 60c is much shorter than the length in the software.  So if I create BigFishHole1 and BigFishHole2 in the software, then download to the GPS,  Both the waypoint names get truncated to BigFishHol and I lose one of the waypoints.  Depending on the specs of your software and GPS, this is something to be careful of.