I did hundreds of these for a Saturday market. I used buttercream mixed with different jams and curds. Use a good large tip, stab it into the center of the cupcake. Fill gently, the cupcakes can burst if they get too full. It is ok if the filling shows a bit. Your top icing will hide it.
I've also seen a method where u can take ur knife, hold it at a angel and cut a "cone" out of the top, scrape off the cake on the bottom of the top piece and fill with filling and then put the lid back on.....and cover with icing...
I hope i explained that ok...if u need for me to clear it up pm me and i will try to find it.
HTH
http://home-and-garden.webshots.com/photo/1111026949051689275GGmuAe This is a website where they take you step by step on how to fill cupcakes and make perfect ones. Let me know if this does not work.
The easiest way to make sure you don't overfill is to watch the top of the cupcake--it will rise and the amount it raises will let me better guess how much fillling when in. If you are getting to much in it will start to crack, but again frosting will hide it!
I fill cupcakes all the time- same method as above. I also have a recipe for cheesecake cupcakes that are done a little differently. You put a small amount of batter into the cupcake liner and bake for a few minutes - until it just starts to set up. Then you place a dolup of cheesecake mixture and a little cherry pie filling an top of the cake. Cover that with more batter and continue baking. The cheesecake center is delicious! This is my most requested cupcake. Doing a BUNCH this week for Valentine's Day!
I also use the tip #230 is really handy
this is a great new website from wilton
http://cupcakefun.com/techniques/index.cfm?category=26
I was just coming to this site to post about filling cupcakes when I saw this thread 
I have a Wilton tip 230 that my uncle gave me along with all his old cake decorating stuff, my aunt told me it was for filling cupcakes but I wasn't quite sure how to do it... glad to read all the tips on here can't wait to try it!
Oooh! I've never tried this but it sounds so easy. Gives me a great idea for Valentine cupcakes for the kids' teachers. Thanks to all who posted tips.
The "Cake Doctor" (it might be the "Chocolate Cake Doctor") has a recipe for filled cupcakes that you add the filling before baking. (I think it's mostly a cream cheese base, similar to a Hostess Cupcake). I havwen't tried it yet, but it is on my list!
I filled cupcakes for the first time last we. I made the White Almond Sour Cream recipe and it came out great.
I made an Orange curd and filled the cupcakes. I put a BC damn around the edge and poured a chocolate ganache over the top.
They were delicious, and fun.
I just made 400 filled cupcakes for an event! I used a bismark tip to fill. Be careful not to put in to much because they will leak and explode! (Those are the ones I eat! 
) I have also used an apple corer! I "core" the top of the cupcake - fill it - and replace the top back in the hole - cover with icing! filled cupcakes are some of my best sellers! I especially love chocolate cupcakes with cookie and cream filling with vanilla buttercream on top!
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