I went from my beloved 8.5 to X1 Studio for 3 months and then to X2P, so I have new toys that I'm terribly impressed with that may skew my judgement but...
X2 is about convenience, I've talked to several people (all longtime CW guys) about it and we've all basically said "why haven't we requested this & this & this before?".
I realize many enhancements have been requested here and elsewhere, but X2 really is intuitive - you can just bumble your way through it and it just feels better to me.
$99 means different things to different people and I do know some that are happily still using 8.5, but just watch the vids and see if it's worth it to you.