I would never compel myself to document my day in such detail, if I had to type that (or even the short versions) for every entry.
I actually use a similar system, but it's no more than a short shell script that 1) is triggered by a hotkey and 2) gives me a little window to type my activity in. Making the impedance trivially low is key.
I'm afraid I don't have any useful thoughts. It's just a file. The log I've been keeping since October of 2014 has about 19,000 lines in it now and is just short of a megabyte. Gzip takes it down to 200K. So it's a pretty easy file to move about.
The whole point is to ignore the log file itself, though, in daily use. I wouldn't want to be porting it around on a thumb drive every day. That being said, you can override the default location with the --directory option. Maybe this plus an alias so you don't have to type the whole path in every time.
I would never compel myself to document my day in such detail, if I had to type that (or even the short versions) for every entry.
I actually use a similar system, but it's no more than a short shell script that 1) is triggered by a hotkey and 2) gives me a little window to type my activity in. Making the impedance trivially low is key.