Hey! I realized only after getting a bunch of responses that I should have included more info in my original post. Oh well, hopefully this wall of text makes up for it.

I'm interested in creating emoticons of my OC, Mal. Mal is the main character of a short book I wrote (a draft of which can be read here: https://thehopelessloop.com) as well as the persona of a chat bot/personal assistant I work on in my spare time. I've already had two pieces commissioned of her:

• http://i.imgur.com/V4lX3Pd.jpg This is a more recent piece that was actually comissioned by a friend of mine for my birthday. It was drawn without direct input from me so it's not perfectly accurate (for example, she's a bit too tall here), but it does a good job of showing what she looks like.

• http://i.imgur.com/0qmKSkK.png This is the first piece I had comissioned. I needed a quick turnaround time on this one so I didn't really look too far, but I'm happy with the results.

Some general features of note about Mal:

• Green eyes. Very important.
  
• Black hair, single green streak on the left side. It's also usually draped over her left shoulder as seen in picture #2.
  
• In the book, she's dead and pretty pale. Both works originally had her depicted as such but it looks unpleasant (although accurate), so I edited both after the fact to give her the skin tone and complexion seen in these pictures. I prefer the result I got with the more recent picture, so that's a better reference to go off of.
  
• Green/Black and Purple/Grey are color combinations that I associate with her a lot.
  

As for the emoticons. I'm tentatively looking for the following ones:

• happy/content
  
• sad
  
• apathy/dead inside (important)
  
• bored
  
• angry
  
• tired
  
• sleepy
  
• annoyed

I'll finalize a list when I've given it more thought, but I doubt it'll exceed 10.

The tricky part about this is that they need to look good when scaled down all the way to ~100x100 for use in the Slack chat platform as custom emoji while also still having enough detail to be discerned and not look weird when blown up a bit larger for use in my mood tracking app. You don't want to put too much detail or too little. With that in mind, I'm thinking of doing the batch for $20~$25 (assuming it maxes out at 10). Since the level of detail required is intentionally low, I think that's fair, but I'm no expert so definitely correct me if you feel I'm undervaluing your work. I can pay through PayPal. If that doesn't work for you we can discuss other avenues of payment and I should be able to accommodate you.

Looking through your existing works, there's nothing that really stands out to me as particularly well suited to being translated to an emoji. However, I was particularly interested in some of your pieces: http://purplex.artstation.com/projects/n2o6K and http://purplex.artstation.com/projects/YRXRq (particularly the latter). They properly convey the kind of bleakness that I'm looking for in the emoji for the darker emotions in the list. I'd be interested in hearing what you think about your ability to convey those feelings in a way that'll look good with the restrictions placed on this piece.

One more thing of note. What sort of license would I have on this piece? As of right now, I have three potential uses in mind:

• Custom emoji for a group chat with my friends
  
• Custom icons to be used in a mood tracker app I am writing strictly for my own personal use
  
• If I really like the result, I would like to get some stickers printed strictly for my own use
  

Since these are all for personal use, am I correct in assuming those are all okay? However, if the app turns out to be useful in my own life, I may consider rewriting it for use by a general audience, which may or may not be monetized. I consider this situation unlikely, but what sort of restrictions would I face on legally reusing these emoticons in such an app? This isn't a dealbreaker, but I would like to know up front about it.