I've tried finding the answers through threads that may have already been made, but I can't seem to find anything...So I apologize if I'm just blind. :C

Firstly, I was curious as to why I only got the first year achievement when I've been a member for 2+ years..Does this mean I need to be a member for technically 3+ in order to get the user box?

Secondly, I got the "Raffle winner!" achievement, but to me that implies I actually won the raffle...Did I? Or is that just the name of the achievement for finding a ticket?

Yes, "Raffle Winner" is for finding a raffle ticket in while posting in forums. As for your other question, technically you should get a Loyalty Box once you hit 2+ years. Did you get the "First Year!" achievement by any chance? That one is retroactive for all users as long as the account is 1+ years old.

yes, I did get the first year achievement which makes me think that because of that, I have to wait another year? I don't know :(

Not sure. Just wondering, how old is your account? You can see it on your User Dashboard (under the Personal tab, just in case). I'm sure that's also the page to trigger account year achievements if you are missing any.

It says I've been a member for 2 years, 5 months, 6 days. The first year achievement is all I've gotten. :(

Yeah, by now you should have "Longtime Member" for 2 years... File a ticket (Subeta tab > Tickets > Missing > Achievements) and staff will help take care of it :)

I had some weird achievements pop up for me lately (and one of them was regarding my account age). They are great at fixing things when you file a ticket - but do keep us posted! Goodluck :)