I got nostalgic and wanted to see everything uploaded up to and including 2014. The "yester" tags in the cheat sheet seem somewhat broken and don't work when filtered out with "-".

The somewhat spergy solution I came up with was:
201* -2019 -2018 -2017 -2016 -2015
But it is clear this is not the ideal or intended solution and it doesn't include anything uploaded in say, 2008 as it says in the cheat sheet only one wildcard can be used so it can't be combined with 200*.

I think the closest to what you want is the search parameter "order:created_at_asc " in your search, which sort images by ID/upload order, I believe. or "date:yester:2020-01-30" for example which shows anything uploaded prior to this date.

But since we can upload in 2023 something that was done in 2008, this is not a proper way to search it, gotta rely on year tags... All search parameters on the wiki, to the extent of my knowledge, only refeer to information "hard coded" on the site, but year tags are just tags, and I don't think tags support any kind of range beyond the wildcard.

I also asked if it was possible to sort posts by year tags, and the admin Earlopain said in discord:

--Earlopain — 26/jan/2023 19:08

The year metatags are just like all the other tags, there is no concept of ordering by them

So I guess it's just not possible to search something made before a certain date through year tags without a script, and searching by upload-date will leave old posts uploaded recently out of your search.

Would this work for you?
date:2000-01-01..2015-01-01

The range syntax section on the wiki "cheatsheet" has been badly in need of a rewrite for years. Most of its functionality is unclear or just plain undocumented. This applies especially to date ranges.

date:2007-01-01..2015-01-01 or id:<580209