I have a fondness for what McKinsey called "crude instruments", something that is almost certainly good enough, and will stop you trying to get ever more precise data.
There will always be an epsilon to conquer; most of them aren't worth the effort after the first couple approximations, and I value accuracy over precision.
We support our 4,500 active users with a combination of a shared gmail support account, admin screens on the core web app, and a tiny globally distributed team.
One day that won't be sufficient, but it's seen us through the first five years.
Our original intention was to automate some of the standard interactions, that we would just manually process the transactional emails 'for a while'. But funny thing is, the human interaction has proved to be a critical and valued part of our service. We’re pretty sure those actual humans will always be part of the service Beeminder provides.
I use TagTime [1] on the desktop to stochastically track where my time goes. When it inevitably and annoyingly pops up when I'm distracted from what I ought to be doing, that nudges me back on track.