In Matt's answer I began discussing with Matt E over several comments, which I think should be written out as an answer.
As Matt pointed out, this is a rearrangement of this conditionally convergent series which is why you have this sort of paradox.
However it was unclear about how this is exactly a rearrangement, as the equities seems perfectly legal - even for a conditionally convergent series.
- $1 - \frac{1}{2} + \frac{1}{3} - \frac{1}{4} + \ldots = 1 + (\frac{1}{2} - 1) + \frac{1}{3} + (\frac{1}{4} - \frac{1}{2})$ is the first step, which is legal as you simply replace the negative terms by pairs of a positive and negative terms, but you don't change the order of summation from the original series which makes this exchange legit.
- $1 + (\frac{1}{2} - 1) + \frac{1}{3} + (\frac{1}{4} - \frac{1}{2}) = 1 + \frac{1}{2} + \frac{1}{3} + \ldots - 1 - \frac{1}{2} - \ldots$ this is where things break, you've taken a conditionally convergent series and changed the order, basically we've performed infinitely many commutations in order to rearrange the series into this order, and that is what breaks the summation.
The rearrangement wasn't very obvious, but it was hiding there with its big sharp pointy teeth... and when you stepped too close to its cave - it jumped out at you and bit your head off.
The series in the question is closely reminding me of the one my calculus teacher used when he first showed us what changing conditionally convergent series can do, although his was even less obvious.