I manage my investment finances with Quickbooks.
I also suffer from a compulsion to over-engineer any solution I implement.
So, once I had worked out how Quickbooks works, I set about constructing a complex (but very accurate) mechanism for tracking my finances. It was a work of art, something which would make any accountant for a large corporation proud.
However, for my own finances it was overkill, and took far too long to actually enter any data.
So I’ve bitten the bullet, simplified the system, and am now in the process of re-entering two years worth of data.
It will be a lot of pain now, in return for significantly less pain on an ongoing basis.
The next step will be to document the (simple !) process so that my wife can do it all for me.