I am planning to make about 50 cupcakes for a reunion party. I want to fill one third of them with raspberry filling. What do I use to "shoot" the filling into the cooked cupcake? How much filling will go into each one? (I'm guessing like a teaspoon) And, lastly, is it best to fill a cupcake when it's warm or once it's cooled? (I'm guessing cool, but I've never done this before. TIA for any help. You are all always so great and helpful! 
Hi,
I have filled a few cupcakes w/pastry filling and reg BC. i use this tip to fill them: http://www.countrykitchensa.com/catalog/product.aspx?T=1&productId=1386 (i found mine at a local cake shop)
I usually do them when they are cooled. I'm not sure how much goes into it, but i stop when i feel the tip pushing out - or the filling coming out a bit. You can definately tell. You can also find this tip at Michaels in the "cupcake kit" they sell from wilton.
HTH
I always fill my cupcakes. I just use a regular pastry bag with a no. 6, insert it through the top of the cooled cupcake and squeeze. You'll know you've squeezed too much if the filling starts coming back up out of the cupcake from the top. I'd say do about a 2 second squeeze. Totally easy!
I just use a regular open star tip - no need for anything fancy. I kind of poke a hole in the cupcake with a butter knife or a really small offset spatula I have first (the one that comes with the Wilton 1 kit).
Definitely fill cool! If they are too warm, it will melt your filling and you'll get a runny mess.
Just like Katskakes said, just fill until you see a little come out the top. It is sort of a feel thing but you can see the cupcake sort of plump a little and you know when to stop.
Good luck!
Hi there, I bought this kit a Michaels and I love it.
http://www.wilton.com/store/site/product.cfm?sku=2104-6667&CMP=AFC-CCF
Hope this works.
I fill from the top of the cupcake never had a problem of braking cupcake.
you can tell when you are over filling because cupcake will start rising, thats when you need to stop.
I actually just practiced filling cupcakes this past weekend since I'm doing a bunch of cupcakes for an upcoming family party this weekend. What I did was use an apple corer to take the center out of the cooled cupcake and used a #12 round tip to fill the well. Worked just great and no breaking or overfilled cupcakes.
HTH
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