Some more raw data; this time from this year's mid-year vote.
2008 MIDYEAR WINNERS
Funniest User - LOLZILLA & AshfordPride
AshfordPride won Funniest User in 2007 along with Master Creator (tied with BlueFlameSkulls). LOLZILLA has also gotten his share of nominations in past years and even this year.
Attention Whore - Gothclawz
This one may or may not be a flavor of the month award winner. He's gotten a couple of nods at the end-year nominations, but there's a couple of names that are getting thrown out there more (although a lot of those names were also nominated mid-year).
Drama Queen - WadeFulp
Wade won the same award in 2006. I guess in his defense he's doing his job. No real mention of him as much this year though compared to others, so I guess only when he puts information out do people notice him.
Never Logs Off - ZeroAsALimit
Only ZAAL and Maus have ever won this award, with ZAAL winning it 3 times and Maus once. Of course now Maus is rather inactive (last post [that can be seen by the general public] was 9/4/08, but her profile does state she'll "brb").
I Miss You - bigbadron
ron won this same award back in 2005 alongside DanMalo. If he wins this year he joins Denvish as the only person to win this award twice. Also, Livecorpse is the only non-mod to win this award in 2004.
Best Artist - BlueHippo
BlueHippo won Best Poster last year. He also has been getting plenty of nods since 2006 for various categories so I wouldn't doubt to see him win again this year.
Master Creator - Elios
He might take it again at the end of the year as he's getting a decent amount of attention in the nominations thread.
Midyear Rookie of the Year - MoriChax
Maybe it's a sign of how Newgrounds views new users that she seems to be racking up nominations by the barrel for the year-end competition too. I guess there's few newer users known, or maybe she actually is a good rookie.
Most Improved - HotActionYiffFur
HAYF won 3 of the worst awards you could win in 2006, only to then win most improved in 2007, and again in the mid-years. I think that qualifies as "improvement."
Biggest Spammer - Mendou
Mendou was 2007 Rookie Of The Year. Unfortunately it seems that the Rookie Award is where up and coming posters go to die as most of the winners are either inactive or now unknown. Tough break I guess.
Most Overrated - HotActionYiffFur & WilliWowza
I guess improving your posts is so outdone. Or maybe HAYF tying Maus for most BBS awards is a sign of being overrated. Funny enough is that both of these guys have won this before (3006 and 2007 respectively).
Most Underrated - Batdan
Again; another person getting a lot of nominations at the end of the year. Although isn't that the oxymoron of this award? Well good luck with the Most Known Unknown Person Award.
Best Mod - Zerok
I think he's onto something since he did win the award in 2007. Too bad he sucks so much lol.
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Worst Mod - Figmentum
He hasn't gotten too many nominations this time around as compared to other mods. Honestly I'm still scratching my head as to why he's a bad mod (inactivity?).
Worst Poster - TomsPulp
I wonder if he'll be known enough to win it at the end of the year after getting deleted? This award seems to signal the end of your posting career too; well except Zen444 who won in 2006 and now posts in VG forums mainly, or WeedClock who posted the other day (first time in like a year).
Best Poster - Gfoxcook
Gfox is still getting some nominations for the end of the year. Maybe he can go the whole year strong; only time can tell.
One of the trends I'm seeing is that the awards do not follow the entire year, as a lot of the people nominated in large numbers now were never mentioned in the mid-years. You also cannot throw out the idea that some mid-year winners are being nominated just due to the fact that people reviewed that thread and used it to fill some gaps. Of course there's always the trends of mods being noticed more for specific awards or ZeroAsALimit winning, but for the most part it really seems that people stick to big events or decently-sized events that just recently happened. Maybe it's a flaw of the system or maybe it's just how things go.