One of the fun challenges I have in my current job is that we provide releases to customers according to the customers schedule (which is related to needing hours of downtime because it's a creaky old system).

Some customers will skip releases altogether making strategies like add a new column, back populate it online, then the next release uses the new value impossible.

I guess that point is slightly moot when it'd take 2-3 releases to achieve the end goal and each release cycle is about a month.