Counterspell says "need to use same level spell slot, or else pass a check."
What check is that supposed to be? Every single time I tried to use a lower-level slot, it just flat out failed. Is there a mechanic that's not triggering, or have I just had some epic bad luck?
You're misunderstanding the text, which is understandable.
You cannot cast Counterspell using a 1st or 2nd level spell slot, because it's a 3rd level spell. What it's talking about is the spell you are *countering.* In other words, if a hostile creature is casting a spell that is first, second, or third level - Counterspell will work.
BUT, if an enemy casts a 4th level spell, you'll have to pass a skill check after casting Counterspell - UNLESS you cast it using a 4th level slot or higher. Basically you need to meet or beat the spell slot level used by the enemy, otherwise it's a skill check to see if it works.