My only concern with the automatic $100 is the workload it may cause
for TOs, but this might not be a huge problem since a) many people
won't bother submitting a claim since it's not worth their time
(automatically selecting those who really need/want it) and b) so far
there haven't been that many requests. (Although you can argue the
latter is because it wasn't documented/publicised properly.)
Of course, it's different if we're talking about bigger amounts, but
for that we have a sprint/mini-debconf process anyway.
Let's just have an automatic $100 and keep the bureaucracy to a
minimum.