I'm actually currently considering commissioning art for a scene that happened in my Pathfinder game, but have partly been putting it off because I don't really know how commissions work. It helps that I go do photoshop edits on art pieces to capture the look that I have in mind (because I mean it never leaves our little group so what does it matter) and I feel presenting that as a "reference" would be a little slimy. There's also the issue of whether to commission "test pieces" like for individual characters before commissioning something more complex.
I have limited experience doing this, but from what I know:
-Having reference helps; in fact, supplying detailed description of the subjects prevents the artist to do character design on your behalf, which can be rightfully added to the bill.
-Using someone else's art for specific features might be a bit weird, but it might depend on the artist. As with most things, having a honest conversation before committing to it is a wise thing.
-Multiple characters can rack the price up pretty quickly, but that depends on the artist's pricing and the money you're willing to pay of course.
-Depending on the artist and the final price of the commission, they might be amenable to do a free quick sketch of characters before delving in the final piece. Again, the more accurate the description is, the less likely the artist is to go off the mark, and the artist may check with you after the basic outline and flat colors (my friend did*) to make small edits. If you ask to redo everything from scratch after following your instructions they might (and honestly should) bill you for it, obviously.
*I had him correct Sharaka's spikes outline and color, the eye color and maybe something else I can't recall right now, maybe the jaw barbs.
Again, the best thing to do is ask a possible commissionee (that a word?) about all that! They may make discounts for bulk orders if you want busts and a more complex piece with the same characters, who knows! Also, backgrounds are often a pain in the ass and/or time consuming, but every artist can tell you that
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I kinda skipped out this week because it's been a lousy week for me. [...]
Oof, that sucks major ass. Glad to know you had the help you needed, and hope it gets better soon.