Originally Posted by MightyLlama
So I tried those regen flasks and they are pretty bad for any support with a heal. They are so expensive I can only get 2 wards, and they give back almost no mana. Even if I was a tank support id rather just get 2 charms.
It's situational. If you're a nunu against a sona lane, you pretty much have to get one unless you play so cautiously that you let your carry get zoned or die. Against lanes that are very low harass, it can be inefficient compared to just starting with fairy charm/regrowth pendant and having your only consumable heal be the biscuit - basically the support equivalent of starting with a doran's blade. Getting to know matchups and getting a feel for how much damage you're likely to take in trades really helps for choosing your starting setup.
As far as Kage's Lucky Pick goes, I usually skip it on melee support if I'm going to need to be part of the tank line unless the game really looks like it's going to stall out for a long time and be one of those 45-55 minute games; if there hasn't been first blood, a dragon kill, or any turrets taking damage by the 15 minute mark, it's a pretty good indication it's going to be a longer game. I love the item on any ranged support that's going to be part of the backline, though - Zyra, Soraka, Sona, Nami, etc.