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Re: OK, so I'm Sanding My Bottom...
If you'll look at the photo of the strainer, it is surrounded by white surface. I think that's your gelcoat. Everything on top of that surface is either old paint, or dirt or algae covered with old paint. I don't think most of the pits you are seeing are "boat pox." I think they are simply many layers of peeling paint. If you get all the red and brown and blue stuff off, eventually you'll get down to the white gelcoat, which is where you want to be. You don't want to remove the white gelcoat.
I wouldn't apply any filler to try to smooth it out, because I believe you'll be filling pits in old bottom paint and dirt, sealing them there forever. You have done a terrific amount of hard, nasty work, and smoothed out the original mess fairly well. My suggestion is that you apply one coat of ablative antifouling and enjoy sailing the boat for the summer, and then, next spring, have another go at it, and finish the job. After it's finally done, if you use no more than one coat of good quality ablative each year, you'll probably never have to strip it again. After you get rid of all that old paint, you'll be able to see whether there really are any osmotic blisters under it. At that time, you can decide whether you need to do anything about them.