I always seem to run into the "will I maintain it by installing upgrades" question before that one. :-) One exception was the case of a certain static website generator which the author migrated from PHP to Python as a natural progression from v.1 to v.2. That was a bit of a shock.

I have since moved my personal snippets collection to plain old HTML. You can do a lot of processing with a capable text editor these days, and in doing this I can save my maintenance energy for projects where a dynamic approach is really needed.