the effort of loading multiple css files stands against the complexity (and hence speed) of parsing as well as maintenance aspects
If certain subsets of the monster file can be related to certain html pages (and only those certain pages) then a separation into smaller units would make sense.
example:
you have a family homepage and your all.css contains all the formats for your own range of pages, your spouse's, your kids' and your pet's pages - all together 3000 lines.
./my/*.html call ./css/all.css
./spouse/*.html call ./css/all.css
./kid/*.html call ./css/all.css
./pet/*.html call ./css/all.css
in this case it's rather easy to migrate to
./my/*.html call ./css/my.css
./spouse/*.html call ./css/spouse.css
./kid/*.html call ./css/kid.css
./pet/*.html call ./css/pet.css
better to maintain, easier to transfer responsibilities, better to protect yourself from lousy code crunchers :-)
If all (or most) of your pages are sooo complex that they absolutely need the majority of the 3000 lines, then don't split. You may consider to check for "overcoding"
Good luck
MikeD