Other countries have made these changes on shorter time frames in recent memory. I don't recall hearing about any catastrophes.
In 2011, Samoa changed time zones to land on the other side of the international date line. I don't believe that was years in the making. Even last year, they announced they would no longer observe daylight saving time; they decided that 11 days before they were scheduled to switch their clocks.
In January of 2015, Chile announced they would keep daylight saving time year-round when they rolled forward in April. Then in 2016, they scrapped that. In 2019, they even changed the dates on which daylight saving started and ended. While this was over the course of several years, they didn't go into this thinking about how to make it complicated for the next four years.
Many of the states don't seem to think this is a serious concern, either. Several, including my own (Kentucky) passed legislation to permanently observe daylight saving as soon as Congress would allow it. I don't think the folks considering these measures are underestimating our ability to deal with these types of changes.