Just a thought but would't creating a new file for each year make it more maintainable? I can't imagine searching a 100k line file or scrolling through it.
Honestly, there's not really anything to "maintain". Just a text file and some timestamps. No magic at all. Simple as dirt. That's the magic :-)
A do see a lot of people who are making date stamped files, but I can't understand why. Do you want to switch between using C-s vs dropping to command-line for grep?