At least up until this point, Winter Bash has had different people leading it every year, at least on the Community Management side and the CMs are the ones who come up with the ideas for the hats and their triggers. The tradition for assigning a CM to the project was to make the newest member of the team run Winter Bash that year. Though there have been exceptions - for example, the year I was hired, I got out of being the CM leading WB by having a baby in October.
That said, most years there's been more than one CM involved, particularly in cases like this year where the "official" newest people also didn't know much about how Winter Bash works, so the team this year was the two new people and two people who know WB more than is healthy.
All of this to say that it's really natural for the "difficulty" of earning hats to vary from year to year because there's no consistent person helming the hat triggers being created. Side note, the person leading WB hat concepts last year was Slate, who's a puzzle master and she came up with some really devilishly hard triggers, some of which were never solved.
As we were working on coming up with triggers this year we had a few things we wanted to keep in mind:
- We should have hats that relate to new features that have been released to get people actually using those features.
- We want to encourage constructive use of the site - hat triggers should lead users to participate more fully and hopefully encourage new people to participate in moderation activities and explore all of the three main areas of the platform.
- We should have different difficulties of hats - some that just require a click or two and others that are either difficult to earn or difficult to solve the trigger for.
- Some hats should build upon others (e.g. Squared Away and Cubed Away)
- We should have some fun! While "we hate fun", Winter Bash is all about having a good time and celebrating a busy time of the year for people. We want WB to be a chance to work collaboratively and maybe get to know each other a bit better.
For completeness, we also had some goals when it came to the event and hat designs:
- Have new hat artwork even if the triggers were being reused.
- Recognize a variety of cultures.
- Hit the memes and cultural references really hard.
- Don't make it only about hats.
I guess for next year we should add, "Don't violate the Geneva Conventions" as a goal for the hat designs.
So... to answer your question, there's no specific goal to make things easier or harder than last year or the previous year... though last year was likely somewhat "harder", particularly on the end of things that are really hard. We do have a lot more click-only hats but we also like giving people a variety of "easy" things to get so they can actually have a few to choose from.