I understand the fully-packed 1 request situation is great for serve-time and page-rank, and after it is all said and done its probably the better solution. This is a slippery slope though because its possible to do too much of that and not enough real work.
The bigger the site, lesser the point in all of this (and harder). It is a small personal site and I enjoyed the process of doing all of this. Makefile is nice to have in the end, which means it was a one time investment.
Unless you have it set up in a certain way - it does require one more step. When you save the content you still have to run the makefile and then upload it. Even though this could be done in a batch script, just looking at the problem you are trying to solve (run a personal site/blog), it seems rather over-complicated.
The virtue and delivery of the idea is cool though - never discounted that. I just wanted to play devil's advocate on the practicality - which you seem to agree that it isn't really practical.
It can also be integrated with DVCS post-hooks.