Don't forget the two who shall not be named! They can be the Kenny's of Heart Song.
Except instead of graphic death, every episode there's some G-rated slapstick at their expense. Like what Twilight went through in Feeling Pinkie Keen!

Alright so Amethyst Star is in as the wild and crazy Tomo esc character. :D

I like Cloudchaser. :(

How about Cloudchaser has improbable luck that rewards her with random awesome stuff, from breaking a water main that starts spouting chocolate coins to a life-sized licorice chariot pulled by robotic neon parrots being the prize in her cereal?

... Okay, you lost me.

Cloudchaser assisted in making Fluttershy cry.

She must atone for her sin.

See, having her in Heart Song can allow her to do just that. :D

You sure?
Because I think they're starting to multiply ._.

And that's Snow Drop. Snowflake is a canon character.
http://fc03.deviantart.net/fs70/f/20...01-d5j7an3.png
He has like, 9 names, but the two most common you'll see for him are Snowflake and Roid Rage.

And I loathe Flitter and Cloudchaser...So much.

Would this be a gift or would I have to pay for it?

Umm... yeah, no thank you. :lol

What if I put her through hell on a constant day-to-day basis?

By having her be Cursed with Awesome. Hence the random awesome stuff happening to her frequently that is never explained and kind of annoys her.
Like receiving a silver pomegranate in the mail every day for no damn reason. Sure you can pawn it off, but WHO KEEPS SENDING HER POMEGRANATES MADE OF SILVER?