At first glance selling now therefore makes sense. But is that so? How big a difference in $ would it really make over the long term? I just created a little Excel sheet to answer that question for myself, with 2 scenarios over 20 years:

I think you are overthinking things. If you like to fiddle (as I do) with your portfolio - you are very likely to find some nice opportunities in the next 12-24 months - and having cash available for those will be nice to have. If you aren't a fiddler then just keep it simple.

Recent Fiddling

* DIS - bought a little in Sept 2023 at $81.85 - (I also bought some in the $130s earlier) - so far "ok"
* DG - was discussed at length, doubled down at $103.11 in October (from initial purchase at $117) - so far "pretty good"

Again this is just in the last 6 months, I am 100% certain that more opportunities will come up again. These last two "fiddles" depleted my cash position; so I sold some BRK and created some more powder. I generally keep about 10% of my portfolio in "fiddle" position and try and juice my overall returns 2% - 5% with this. Its worked out well the past 10 years or so; making 2-3 investments per year.

5 YR : $18.08% vs 14.76% (Index)

Note: I keep ~50% of my portfolio in the index, and ~15% (or so) in BRK.

tecmo
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