I'm team time skip forever! Or possibly team "I'd rather talk about this so lets pop in to a couple short snippets of things that happened between x and y, then let's focus on thing y."
Using real timelines is hard! In my holiday story, I knew it made more sense in 2000 based on what they were up to at the time, but I just didn't want to deal with the fiancee issue, so I picked 1999. You're brave for being as realistic as possible!