I would trim all cases after first firing just enough to get them all the same length and possibly cull any very short cases.....eg FC brass.
Overall case length and how that relates to the chambers maximum length depends on the reamer used in that rifle and is nothing to do with headspace or jump to lands.
I personally would mark brass and size for each rifle as required.
If brass is to be used in two different rifles with the same load then basicly you are going to have to size and trim for the tightest chamber which WILL stretch your brass in the looser one and cause these cases to grow lengthwise and if the difference is more than a little case head separation is inevitable.
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