The problem with "total number of maps" isn't really helpful because no map is the same. Unless you redraw over and over the same map only then can you really see a marked improvement. If there is something in particular that makes your maps "bad" (style, technique, positioning, etc.) that isn't to say it will always appear in every map you do. Similarly drawing a top down battle map in comparison to drawing a region, city or world map... they all require different techniques and levels of knowledge (you don't have to know how rivers run when drawing a battle map).
I've used Photoshop for 15years, I've never really been a digital artist, but always used to make little nifty things for myself or graphics for the guilds I was in/ran in various MMOs, or digitally manipulating pictures of friends, but never anything serious or any large project. However, in this time I learned to use the tools of my trade (though only to a basic level because some tools I never needed for the things I was doing), learned how to use layer filters and learned a few tips and tricks to try and get things to look how I wanted them.
About 4 years ago I started doing a VTT tabletop game and I was making the battlemaps weekly, here I was pretty much taking images from RPGmapshare and Dundjinni and making my own maps from them, editing images I found to make my own objects, etc. and for three years this is how I made my maps, using the techniques I had learned, applying lighting sources to make a map atmospheric, etc.
Last year I started running a D&D campaign and simultaneously started working as a freelance illustrator with a regular monthly paid job, but decided I would try to get into some map design work as well on the side. That's when I found this place, that's when I stumbled upon the works of Mike Schley and people like Torstan and Djekspek who did hand drawn illustrated maps and I pretty much hit the reset button on how I wanted to design my maps in the future, completely shifting away from the Dundjinni style maps and focusing on hand drawn maps. One of the major things that made this possible was that when I found this site, and got my new job, I also got an Intuos4 XL (A3 sized Wacom tablet) and up to this point I'd never used a tablet in my life and had always used my mouse to drawn. This was a major step because I could now draw handdrawn maps straight to digital with a major added bonus: pen pressure. It is ridiculous how much better all my illustrations look with this single accessible feature and how much it has changed my map drawing.
If you check my Finished Maps gallery you'll see three maps. The first shows where I was at making digital "maps" (the night camp was an isometric map I was trying, which looks more like something from a Dragon Age type RPG) but demonstrates my "level" with photoshop proficiency pulling together all sorts of elements other people had made and editing them. The second "town gate" is my first ever hand drawn battle map, the third is the first time I ever hand drew an isometric map. Now, trying not to come across as arrogant, but I'm extremely happy with how both came out and think they are easily of a professional quality... but these were my first hand drawn maps. So in response to your original question, how many maps did I draw to achieve that level? None. Does that mean that someone just picking up a pen for the first time and drawing their first map will be able to do it the same quality? Of course not. However, I'd learned so so much prior to this point doing other things and picking up tips and ideas and methods on how other people do their maps.
So unfortunately there's no real way to monitor "okay I need to do X number more maps and I'll be better". Keep drawing, keep posting, keep taking the constructive criticism and work on it. Be careful of the advice you take because people distribute it freely, but there are some over others whose advice is always well worth taking (take the advice of the Chef who cooks the gourmet food, not the food critic who doesn't know how to actually cook himself). Maybe try smaller projects so you can churn out more stuff instead of world map after world map; working on a continent where you still get to experiment on forests and mountains and coasts is more useful than drawing a world map and just repeating the same mistakes throughout the entire piece. Finally, maybe try mixing things up, do a city map, and a region map and a battlemap and check out the work of people you admire and even trying to mimic their style will improve yours until you find a style of your own.
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