So it seems that during my upgrade from Win7 to 8.1, my timezone got set to Pacific. This, of course, would probably destroy any time based encryption (or ssl / handshake / cookie seting) simply because it would be out of sync.
Further, when I changed it to my local time zone, it happily gave me a +x hrs thinking I was simply changing time zones.
The solution:
Change to proper time zone, resync with time.windows.com, clear cache and login again.
I appologize for the error on my end. It was an oversight due to... well... ignorance I guess.
Thanks for looking into it :)
Ryan