Now, decades later, I get it better. The number 0.99999... is 9/10 + 9/100 + 9/1000 + 9/10000 + ..., which approaches 1 asymptotically the same way that 1/2 + 1/4 + 1/8 + 1/16 + 1/32 + ... approaches 1. Under many circumstances, you can treat that number as if it was 1, which neatly answers Zeno's Paradox. (Though beware of the limitations of that analysis: 1/n approaches infinity as n approaches 0, but 1/0 is not equal to infinity. Because 1/n approaches infinity only as n approaches 0 from the positive direction. If you look at the sequence 1/-0.1, 1/-0.01, 1/-0.001, etc. where n approaches 0 from the negative direction, that approaches negative infinity. A function that has two different limits as you approach the same number from two different directions cannot have its limit substituted like that).
It really comes down to what semantics we attach to "=" when one of the sides is an infinite series. The "equals to" sign that we have used prior to that mental exercise was for finite terms only, we had not had to deal with infinitely many terms before that leap in thought. So now we have to extend the notion in a way that is backward compatible.
A convenient one is it is equal to its limit if it exists.
I would say that the semantics are about what an infinite series itself is, not about the equal sign. Once we have the common analytic notion of convergence of an infinite series, then the equality makes sense. The issue is that an infinite series is not an actual sum, but, formally, it is a sequence (of the partial sums). As you say, we represent the limit of the sequence of the partial sums with the same notation and only in the case that we have absolute convergence, but that's basically because we use the same notation for two different things (the sequence of the partial sums, and the limit of that). If we know we refer to the limit, I don't think there is any semantic complication with the equal sign.