Great discussion. Keep it going. Just one thing I wanted to reiterate and add my opinion,
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What about trimming the envelope to only contain the cancellation stamp? Not really pictured, but I have MANY pieces of envelope that only contain the cancellation stamp and the postage stamp. They sure take up far less physical space than keeping the entire envelope.
I think you sort of answered your own question,
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What I don't want is to sort through it all with a certain line of thinking, only to decide later that I want to go a different direction. So I really just want to formulate a plan (that's logical, reasonable, and doesn't destroy potential collection value)
Cutting the stamp and cancel off the envelope would reduce the volume, but also reduce the value. "Value" could include either monetary value or historical value. I love the story from Parcelpostguy about tracking down his father's old addresses from the otherwise worthless first day covers. If your letters are from within the family, I say keep them intact.
I also enjoy seeing the return address on old letters to see who my relatives were communicating with. If you simply tear off the stamps and throw away the rest then you lose all that information which could become meaningful someday. That said, if these are just boxes of ordinary and modern mail hoarded from various sources outside the family (buying from an estate sale or scavenged from a corporate recycling bin), then there may not be much historical value worth saving.
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Your First Day covers don't have a cachet (image on left half of envelope related to the stamp subject) so those could be soaked off.
Sure, the value of an addressed un-cached FDC is minimal, but still they can be sold at a stamp show bourse (or at a garage sale) for ten cents each, versus the soaked stamps worth a penny a piece. Or give them to a 4th grader to include one in a school report about a historical subject. (Do kids in school still write reports today, or is everything done on the computer?) I did give my nephew a first day cover once that was cancelled on his birthday and he really enjoyed it. In other words, the uncached addressed FDCs have minimal value to an experienced collector but still have value to non-collectors, and could possibly spark a non-collector to become a collector, so keep them intact. IMO. :-)