Does it bother you when you need to spend money on CDR when you already reach the CDR cap?
Especially, now we get another 20% CDR item. 
You want to get more of the utility items but the feeling of spending part of your gold for nothing.
Other classes now have more access to get CDR after their rework. I think support itemization should give something else other than more and more CDR.
You aren't building right then.
I hardly ever build 
on supports anymore, you're practically guaranteed to be at or over cap even without them if the game lasts past 20 minutes.
Sometimes I think about building them early and selling them for other boots after I have 40-45 CDR without them, but supports don't have that kind of money.
feel the worst with half the CDR cap on a single item. I really wish Riot would refocus more of their power into other stats so that they don't make you feel bad about then building more than one of 
or 
(almost all of the gold-generating support items give at least 10%, I think the only exception is 
which is not viable on all supports). Even 
has CDR now, if you're one of the supports who wants it.
is a great item for several mage-ish supports, but puts a major pinch on your build path.
Sometimes it does. But I create pre-made item sets to plan ahead for the CDR cap.
No.
Getting items anytime during the game is a luxury, and I should be grateful for even finishing things.
Though you can always plan things out if you're that worried.
Yes. It does depend on the support though. When I play morgana I generally end up with about 55% CDR in items. Sometimes even when the situation calls for it, I'm reluctant to buy frozen heart because I know the CDR stat usually goes to waste (i usually man up and get it though ;) ) Before 6.9, I ran scaling CDR blues on AP supports but seeing that almost every core item gives CDR out of the wazoo, I've opted to run flat AP or scaling MR depending on the matchup.
