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Hmm.
Well the crank arm seems solid on the BB, just the bolt is loosening. The BB probably needs to to be replaced as well.
Upgrading the cranks and BB isn’t on the horizon right now.
Verbs_&_Nouns-
Well the crank arm seems solid on the BB, just the bolt is loosening.
Do they only feel solid when you tighten the bolt or all the time? If the taper is misshapen as per @Pifko suggestion they will feel solid when you do the bolt up but it’s just pushing a square peg into a round(ed) hole so it has no staying power.
If the bolts loosen and the arms are still nice and solid on the axle, how much can you tighten them? I can always get at least 1/4 to 1/2 a turn on the bolts on square taper cranks any time I try.
M_V
Sounds like the cranks are on their way out. Once the crank has loosened and been ridden on - the square taper will deform more and more and as a result will start slipping again in short space of time. Take this opportunity to upgrade to Hollowtech II?