Wouldn't that have been taken into account when the $12.5 billion was allocated? Or was the $12.5 billion just meant to be the first allocation and they knew substantially more would be need later?

A century? Since 1926? The FAA was created in 1958.

I'm hearing some discourse about "outdated infrastructure" and increasing investment because most systems are analog and not digital.

However, this failure mode seems more likely to be caused by digital communication systems and an 'upgrade' (with commercial incentives) to newer technology.

My bet is that if short-wave radio transmission keeps being used, availability will be higher than stuff like Github.

The DOGE/OMB rampage didn't help either.