Welp if you feel like doing a 12 winner, making something like 1 person a month could be an actual idea but....i feel like for those who would be month 10-12 it wwould be a VERY LONG wait., sure its free but still it does feel horrible to wait a year for an art.

still its a nice art style and like i can understand the concept, giving you time between comission to do it once a month sounds like a good time management.

What i could propose as an alternative would be to make much more simple art like black and white , sketch or i dunno chibi and put more winner slot, the art would be quicker an easier to pump out and there would be more winners. But i see you dont usualy bother with different art format so maybe this idea is just stupid after all...but hey...thats just an idea between other ^^

Its not stupid - Yes I dont bother with art unless its fully done 90% of the time... 98% of the time. That's just my personal habits ^^

I guess I dont consider a year a long time because from my side of it I am getting something every month for a year and I have actually waited 5 years for a piece so I have a little patience XD

That was another reason I thought about letting the winners choose the month they wanted so if someone WANTS a Christmas picture then it was their choice to wait until December.

And on the other side of it - If getting picked first puts you first in line for January (or whatever moth this starts as I dont know when Ill actually hit 1k) Shouldn't 1st place mean something? If every one is getting the same object as the prize I feel like being drawn first should mean something somehow, idk, and Ive never seen a Raffle with 12 winners before so I guess I think its kind of nice to get so many chances to be a winner even if it might take a while to get to you?

thoughts

I think the easiest route here, would be to hold a raffle with 12 winners. Then in order from 1-12 assign each a month. EX, the first raffle winner will get the first month then the 2nd winner will get the 2nd month. So on and so forth! I think that would be the easiest and less stressful on you!
Personally I don't think it's a bad thing to wait SO long for FREE art. In my mind you were privilege enough to win. But hey, that's just my 2 cents

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Thank for your thoughts ^^ that may be the way I go in the end

If you go that way then its the best way in my oppinion, knowing the mass they would all fight for the sames months and youd end up disapointing people and maybe even get stress and negative comment to a degree of stupidity you rather avoid xD.

Actually so giving them an absolute order, winner 1 get 1rst month and so on, is better, its impartial.

I think maybe start with 5 winners. Talk with a couple artist if they would like to be apart of this and that pieces would need to be done within the month. I think it would be a great idea. And getting the artist ok before it starts would be great.

Anyone who gets free art should be happy to get it at all. Doesn't matter how long its going to be get it cause they didn't pay shit for it.

but good luck love <3