Diminishing returns and the fact that you have to pay additional costs with your own time and life which is exactly what you are trying to most efficiently manage and extract the most from.

Improvement comes best from low hanging fruit, something you can implement with little cost which helps tremendously. Basically, a different way of doing things which results in major improvement. Always keep your eyes open for new ways or processes and don't get too dogmatic in your current system.

Next comes those trade offs that have significant costs but are offset by a good margin in the improvements they bring. If there is significant positive net gain, then that's a more efficient way to do things.

The road to obsession comes in an effort to make everything perfect. When one starts making inefficient choices in implementing systems that merely patch a current worry about a system or neurosis. It's the control and "build the best possible box" trap as opposed to finding the box which best fits your real needs and getting comfortable enough with it so that you can use it and move on to enjoying yourself. The mind will always find chinks, it's nature is to troubleshoot and it will find it in whatever systems you put in place. This becomes a matter of evaluating and then implementing only what improves your efficiency rather than getting all twisted about letting your system run you.

It's natural to fall into this trap. I suppose it's healthy to do it because you learn but it's unhealthy to spend too much time on it and torque your life over a prolonged period (precious commodity). Probably a natural process. It's kind of like the crazy diet person who isn't overweight yet measures everything with ridiculous accuracy to a fraction of a gram - that type of obsession is what it took them to lose 100lbs in the first place or worse and more to this point, someone who now needs to do it to feel good about themselves. Find the balance you need in life, re-evaluate and re-balance as required.