Like with accelerating productivity gains, the actual wall clock start-to-end time is mostly unchanged if you wait with starting a project, you can always catch up, why does it matter if I do most of the work in the beginning of a project, or toward the end?
Changing vendors is a pain in the ass, especially in B2B. Like case in point, Confluence has been around for 20+ years and still doesn't have a working search function, and is comically useless it is at everything it does. Yet businesses all over the world are all in on that garbage.
Holy strawman batman!
Wouldn't you prefer confluence fix their search now rather than hold off until the can fix it perfectly according to your end-all-be-all spec (that'll be invalidated after 2 weeks of actual use anyway)?
What I'd preferred was if they took the time to implement it correctly from the get go. What they built instead is of no use to anyone. It's a search function in name, but it doesn't provide useful search results.
Search is hard though. From how it's behaving I think they're just sticking the data in Elasticsearch or Lucene or some such, without having done the long and arduous effort of then making it good.
Though my point is that even though confluence has a search function so broken they effectively don't have a search function, they aren't meaningfully bleeding customers over it. Business sales are incredibly sticky that way. Regardless of what pleases me as a user, Atlassian has no real incentive to fix the problem, and evidently hasn't (at least last I checked).
Which is why I consider it better to use the tools that I have today to make a feature that is good enough. Rather than cynically leaning on some vendor lock-in to hope the customers stay.
Given that you seem to consider Atlassian's software so crappy, it's a bit confusing that you bring them up as an example of good management? Your advice is basically, write crappy software and don't spend any energy improving it, until you can do so for the minimum cost.