I realise I’ve been on a bit of a Pokemon bender recently. I swear I’ll get back to serious drawings shortly, I just needed to flush this all out of my system!
The other reason I’ve been doing a little more fan art than usual is because a local pop culture convention is coming up and I’m going to try my luck at arming an artist table there. Whilst I’d love for my original characters and pieces to be the main selling point, I also realise that you have to play to your audience (it does help that I do love Pokemon and comics though).
mechanicalpen 
Good thinking with prepping a supply of Pokemon works for sale at a Pokemon event. But, is it okay to be making money off drawing characters someone else created? And, do you need a license to do so?
I’ve been a lil Pokemon-obsessed in recent weeks after hearing about the 20th anniversary. But, my creative drive has been Surfed over by a lil lazy game time, getting back to my LeafGreen and Emerald roots. It would take me months to put together a modest collection of pieces I’d feel fit to sell.
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That’s an interesting, and hotly debated, point you make about selling fan art. You are right, and it cannot be denied, selling works (even if hand made) based on some person’s/company’s IP is a copy right infringement and these people hold the right to sue over it. That said, the number of times these larger organisations hunt down smaller creators (and in most cases, big fans of the original content) is few and far between. Why? Because the fan community, who are the ones buying the official products too, would see the persecuting as a bit of a jerk move. In turn, this negativity would detract from the appeal of the company as a whole.
Does the “others are doing it so I should be able to as well” argument really hold up? Not really, but you also have to look at the whole context. To just buy a table at these cons cost around $200+ so even if I sell one print alone (whether it be based on one of my original ideas or an existing franchise) I’m still at a loss. At the end of the day, I can morally justify the act to myself of selling fan art so long as a) I don’t claim it as an “official” piece of merch, and b) so long as the fan art I’m selling makes up less than 30% of all the art I’m selling. At the end of the day, if I get caught out and finned, I’ve understood the risks and have to face the punishments.
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Yes, I know fans making art helps promote the characters/companies in a way. But, I ask myself, do I want people making money off my ideas, possibly coming up with more impressive ways to use them and make more money than I make from them? I should not be so materialistic…but it doesn’t feel right for someone else to get rich off my ideas. So, out of respect for the works of others, I cannot properly get paid for or advertise my ability to draw the works of others without the permission of the original artists. And, when I do commissions (as they are often called), I do so discreetly. I am doing someone I meet a favor by drawing them a character they like. But, I would feel oddly guilty for selling multiple prints at some fair…unless, for example, Marvel Comics wanted me to attend the event to do so.
I once tried to set up a “shop” at a fair without paying for a booth and got an earful of warnings before I stopped advertising myself. I have never tried that since.
You may end up at a loss, but it is only right to pay for space at an event requiring those sitting around selling stuff to do the same. I’ve attended art fairs and mass rummage sales and talked with vendors about what brings them or deters them from renting booths. They all weight the odds of selling enough to make it worth the trip. No one wants to travel across the country to set up shop and go home in debt. So, do the math ahead of time. And, figure out, as you started to do, what sells best and will guarantee profit while also being open to trying other wares that might open new markets in the future.
You’re better off, maybe, advertising yourself as a commission artist than setting up shop without paid permission.
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