I could see this happen in a few years, because it does require a minimum of hustling skills that she doesn't have. Right now she lacks confidence and is extremely socially awkward. That's why I'm trying to find a way to help her make money online, where she wouldn't have to deal with anyone in person. Once she gets a few orders in I'm sure it'll build up her confidence and then she can start going to events and stuff...
Honestly, you've been given FANTASTIC advice with the wedding planner etc. suggestion. Try to think outside of the box a little bit...
She is socially awkward and not that great at selling? So what??? Contact the local business professor at your nearest college with an MBA program. Find a picture of the professor and turn it into one of her pieces. Send it to him with pictures of her drawing it and a kick ass sales letter saying something like:
Dear Professor X:
My lifelong dream has been creating a business selling my art to buyers. I was thinking about (Pitch idea with wedding planners) or (pitch another idea). Would you be interested/willing to pitch this to one of your MBA classes as a project? They would gain the experience in starting a business and I would get the much needed help!
Obviously you have to dress it up and use your best copy writing skills.
Or you could put something on craigslist that you are looking for a straight commission sales guy.
Or you could find a distributor to wedding planners and see if they would be interested in putting her work into their sales funnel for you.
Have her do a drawing of a portrait of a local hero/mayor/etc. and arrange for it to be given at the awards celebration. Then publicize in exchange that she does once in a lifetime commissioned pieces for $2,500.
Once you hit a price point above $500 it's not about the money anymore. It's about HOW you sell it. Think about the fringe benefits the buyer is getting luxury, once in a lifetime piece, exclusivity etc. etc.
THINK OUTSIDE OF THE BOX!