I update a spreadsheet twice a year which takes about 15 minutes. Tracking investments day to day isn't healthy imo.

I agree, generally. But there is always a bit of a nuance when it comes to personal finance. I have gone through the full cycle, I started off with logging every single transaction, then syncing everything and tracking monthly cash flow, investment dashboards and then to yearly syncs and now I barely think about it.

What happened was I slowly built an awareness of how things are going, where my spending and savings are and internalised a few things. For example, as a contractor I responsible for my taxes, so 30% of my invoice goes into a savings account as soon as I get paid. But, that wouldn’t have happened right away for me, if I have never done the monthly cash flow.

I think everyone goes through this journey. Because I often see people super into accounting for a couple of years and then completely abandon it later in life. Looking at it daily in early stages help get a feel and set expectations for the long term. Some people get sidetracked here and the phrase “Beat the market” grates on me for that reason.

That's kind of just a brag about being wealthy though, isn't it? For many people who are trying to get escape velocity to being financially secure, tracking spending + investments is a necessary reality.

No one is saying it's healthy but if you have debt, can't save or don't have investments on track to meet your future needs then what's more unhealthy, monitoring or lower living standards?