Annie is getting boring to play.
What do I do?
What do I do?
build Ad annie.
Annie boring... who knew. Well, lets think of a champ played midlane and kills whatever gets close enough to it and almost cant miss, scaleds into late game... hmmmm... In less your trolling Syndra should be good.
Play someone else? I mean, she's a 450 ip champ..she's really meant for beginners with her basic kit.
I need her to climb to silver league and possibly gold.
Slow down your climb rate but don't lose LP by going into an aram or normal draft and play some one else. Then ranked grind, then break again. rinse repeat.
keep getting annie skins until you run out of them to get and then beg riot for more annie skins
Its time to upgrade to 
Ultimate late game 1 vs 3 power; decent kill potential in lane in Silver.
Or
for some serious lane dominance against the inexperienced.
I bought Vlad, he didn't feel as strong as Annie.
Its a bit of a different play style but I find he can usually accomplish a lot more in longer games.

Absolute power once you are at 3 items. He can just run in and 1 vs 3 if you know how to Tides of Blood and make use of all abilities.
Tried a build like this, but it's like you said. He has to go through an extremely weak early game.
play her support?
Play a champ that actually requires some degree of mechanics. There is literally nothing more to learn on Annie after about 5 games of playing her. Edit: I'm looking at your match history and just HAD to say flash is a must on Annie so idk wtf you are doing with teleport heal. Go flash ignite. Also stop building Rylay's, it's useless on her compared, since your goal is to BURST