The only thing I disagree is the title. And maybe number 3; estimate is needed for pseudo-reassurance and comparison; it's ok to not be accurate. And don't spend hours to be accurate.

Agency prison is often overlooked, a superset of vendor-locks. When google domain was sold to squarespace, lots of people complained that they can't pay manually; it seemed unimportant to domain ownership, but they moved to cloudflare anyway; they were forced to migrate, freedom was taken, it was hurtful.

Maybe I'll add - simplicity the author referred to (or I would prefer to call it process elegance) needs experience and knowledge. For no 4,5,6 especially.

The history - surviving or not - contained often overlooked wisdom. Looking at the past reveal that our predecessors struggled the same struggle. It's also wise to realize that time can be too scarce for that; let others that have done teach us; keep our mind open.

Good, elegant article overall.

as always software development is 50% magic and 50% science