Hey, folks... follow-up time!
I tried all of the advice in this thread and (unfortunately) nothing worked. So I decided to take matters in my own hands and get to work. I experimented with a few various letters of the alphabet worth of my contacts. I went to
Sign In, deleted the Live/Outlook contact fully and then created a new version. I then linked them to their appropriate social networks, etc. Then finally I went on my phone and synced the Windows Live account.
VOILA. The contact synced over perfectly.
So I then went one by one thru all of my contacts and redid each contact. I now have all of my contacts synced to my phone. I'm not sure if I do a hard reset, if it will stay (I've taken too much time to risk it!) but hopefully it does.
Hopefully this can help anyone else who needs it. Luckily, I don't have a crazy amount of Live/Outlook contacts... it may be too much if you do, but it's definitely worth it to finally have all of my contacts!
NOW, why this fixes the problem is what is weird to me... maybe Microsoft changed something in their contacts display protocol? Maybe because I had originally imported my contacts from Google to Live a LONG time ago is what made certain ones appear and not all? I can only speculate... but I can't figure out what it is.