It's not petty at all, as a general rule of thumb if you're worried about losing something, then you probably shouldn't be sending it.

Not familiar with Bone Thugs N Harmony, if I'm writing to bands or musicians then I'll try to make contact through email with someone at the record company or a venue to try to get a sense of whether it's likely to get passed on before sending.

An alternative to sending a CD sleeve is to drop an image of the cover you'd like signed into Photoshop or Paintshop Pro and save it with a white border at the right scale to get printed as a photo (I generally do them as 5"x7", which reduces them very slightly, but they come out as quite a tidy shape). That way you don't risk losing the CD cover, and it also doesn't matter if the image is generally dark because there's plenty of white space for them to sign on.

I send out CD Covers all the time.
But before I do, I check on Amazon.com to see if the CD is available at a reasonable price and I buy a backup copy just in case. Also, dont send out rarities - things that are rare and hard to replace

If you really like them, do it. I would try three four times before giving up on someone I like.

I hope this helps.

I know it seems kind of petty saying this, but I am planning on sending a letter to Bone Thugs n Harmony along with my own personal CD cover of one of their albums in hopes that they would sign it. I sent something to another celebrity and it's been almost half a year and haven't got it back yet. So I just don't want to waste my time and lose my cover. Also because no one has had any feedback on them.

So yeah, before I send it out, do you think my chances are high of getting an autograph on my cover? I sure as hell hope so.