I'm a bit confused reading through this thread on what feedback would be most helpful for you. Since you seem to be fishing around for a good business model to take advantage of your artistic skills, maybe the following would be helpful from the perspective of a frequent consumer of game maps and location art.
My background:
- I DM full-game sessions once per month.
- I use a home-brew world in my campaign.
- I've published a few small adventures and drop-in locations, but am much more a consumer than creator.
- I buy far more gaming stuff than I'll ever use. Part of the hobby is creating. I also like to have stuff I like ready to use rather than searching for content at the last minute.
- I've spent a lot of time and money on map software (Campaign Cartographer and its various add-ons, Hexographer, Dungeonographer, Cityographer, plus some niche software from Kickstarter). But due to limited time, I've been spending more money on pre-made maps than creating my own. I'm not going to go into my software spend here, since that wouldn't be helpful for your pricing.
My game map/art consumption:
World Map: USD 500
I commissioned a high-quality map for my campaign with an artist I contacted through the Cartographer's Guild. The high-cost is that this was a bespoke creation based on detailed specs given, some crude mockups I made, a consultative skype call, and several rounds of revisions. I printed it out with a plotter printer and have a poster sized version hanging in the game room, which I can use in game.
I also have high-res visual versions that I can display on a plasma TV display that I use with Realm Worlds. Also, because the image is high res, I can cut it up and create nice looking regional maps from it.
Patreon: About USD 10/month on map-specific content. USD 30 if I include En5ider, which has some map content.
Forge Studeos: Estimated averate of USD 4.50 per month ($1.50 per map/illustration, 2-4 maps per month with bonus game-materials when they hit milestones)
https://www.patreon.com/user/posts?u=2863325
Each map has a grided version, a non-grided version, and an illustration. It is a great deal for and I highly recommend it.
Jared Blando: USD 5 per month
Professional, beautiful, evocative battlemaps by the same guy who made many of the maps in WoTC's publications. For USD 5/month, I get a full-resolution 30 x 24" full color Encounter map the first of every month. Each Zip file contains two versions of the map, both an ungridded a 1" grid version.. Each map is a 300 dpi HQ Jpeg for use in VTT, or for print.
En5ider: USD 20/month. USD 5 per supplement or adventure up to 4 times per month.
Most of what they print are not maps, but they do print material with maps. So, not sure how useful this is for you to look at. I don't *think* I'm missing anything. I think they will go up to six items per month if they hit their next goal. I've been very happy with En5ider, if they go to more than 4 items a month, I would need to revisit what my options are for selecting items to support. Their is a lot of variety and it varies from I LOVE IT to meh. If I had the option to avoid crunch articles, like character class varients, I probably would. I prefer the adventures, drop-in locations, campaign settings, magic items, monsters, etc. Basically everything except character options.
DriveThruRPG: USD 15-30 per month, much of it on map content.
DTRPG makes is difficult to filter on prior purchases. So I can't easily determine my 'map' spend. But for shopping, you can easily filter on map materials if you want to get an idea of price ranges.
Catographer Digital Copies of Official AP Maps
Example: Curse of Straud Map Bundle by Mike Schley: USD 30
Eventually I plan on running Curse of Straud, so I bought this map bundle. Some of the maps will be used with Realm Works and for those that are appropriate as battlemaps, I'll print on a plotter printer.
Mike Schley sells digital versions of his CoS maps that you can print or put into a VTT, which I purchased.
VTT Bundles
I only play in person and don't like to DM using a VTT. But you should look at the various options for selling content for Fantasy Grounds, Rolld20, and similar programs.
RealmWorks Content Market
Someday "soon" this will go live. When it does, it will be another avenue for artists to sell their content. I would by map material from RW before any other source as it would save me time. While it isn't available for you to sell your content there now, you should subscribe to Lone Wolf Development's e-mail list so you know when it is available.
Hope this is useful.