That 60 year caulk I got only lasted 2 months,
There looks to be a lot of movement in that T+G. Are the back sides and ends sealed? Exterior wood is susceptible to changes in humidity, and can swell and shrink with the seasons. Caulk is rated for some expansion, but most caulks - and paint - can't expand that far -
*(Shermax Elastomeric caulk is better than most - something like 70% joint movement).
Since you've already caulked, I'd be tempted to just caulk and paint it again and see what happens. Looks easy enough to re-do.
While I was doing that, I would mention to the customer that it might happen again... because wood likes to expand and contract. I would think it would be less noticeable next time, and if they keep up with routine maintenance could be done again down the road.
Caution: over-filling the joint may cause it to bulge out visibly, at times when the wood expands, or worse, to cause slight buckling in the T+G.
If it were me I would caulk and paint one more time, and then be on my way.