it's hard when so many people are simply willing to play with grey plastic.
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Issue comes down to doing what you like to do. Really if you want to commission paint you have to really like to paint models. If you don't - or get tired - then dont do it at all. You will just disappoint yourself and your client. And you have to be prepared to get a lot of crap too. It is a real pain in the ass process that you have to really control you time and effort to make it worth wile. It is just like any kind of art commission and it ebbs and flows based on the economy, game strength, etc.
I mean - truthfully Brandon your pieces should be starting at $150.00 each for the basic stuff and even more. I know some of the high end Golden Demon winners charge a lot - but if you break down an hourly rate on what they did - they make jack. They have to because they need to ensure someone buys it. It is hard to say - well this FW Angron figure is going to be a 1000 dollars based on the amount of hours I put into coating him in a paint to make him look decent.
But it is sure a hell of a lot nicer to play with painted models. I am lucky in that I have some consistent clients that pay me monthly to paint up their plastic crack that I don't push for much new stuff. Plus I like to get my stuff ready to go as well. I set the hourly at $25.00 as that is what it takes for me to at least feel good about using that time instead of hanging out with my wife or playing a video game to wind down. Too bad I don't get to paint at work anymore as I was able to double up my time. But oh well - the dream can't last forever.
I think the meat and potatoes are where I'm struggling most to find a balance between what feels good price wise, and what I think people are willing to pay, but it also helps my speed for army painting, so I roll with it. I've got, for the most part, my price for custom pieces and display stuff pretty close to what it ought to be. If I could pick up a sword or a crystal brush, I'd probably bump my prices again.
name recognition goes a long way. I don't have to worry about it with locals, but there are people out there that want other people to know where the paint job came from, or discover someone based on a larger award, and that can generate higher prices. You are right in that my work (or that of anyone else) speaks for itself in this niche, but air jordans were only air jordans if they had the logo, amirite?
I think you also expand your audience after winning such an award. Then there's a larger pool of people that will pay the price you want to make.