Oh man that's a long wait for a painting, especially if it's for two separate people. Hope you're not getting any flak from the person you're sharing it with. Don't think restarting it was the smart thing to do on the artists part and offering more art to compensate for the lack of it is also never a good move. I hope this can be resolved soon.
That being said, I am a little bit confused about the raffle. The post on fA says "this YCH will NOT be "first come first serve" but rather randomly chosen from the list of entries for the slot! ", but in the second screenshot you two are talking as if you were picking a winner by hand, so which one was it?