Are you sure you need to take the thinking that far? Sure, uploading map backgrounds could expand your market, but only if you really wanted it to - and it doesn’t seem like you do. The addition of a feature doesn’t necessarily make everyone in a different market come and look at yours for alternatives - you’ve got to do all of the branding and positioning you mentioned in your post.
I’m only saying this because I just discovered the tool and it’s almost exactly what I was looking for. A quick way to whiteboard/wetboard a map together with movable tokens and essentially just theater of the mind with a visual aid. I can’t stand all the complexity and crap that Roll20 or another virtual tabletop tries to inject. Talk about heavy and not user friendly.
I think OP makes a good point in saying that many folks have map images easily accessible, and it’s not difficult to quickly find one that works. Often I’ll just open the PDFs I have of the sourcebooks and grab a screenshot.
Furthermore, you could make the argument that not being able to upload map backgrounds actually decreases Schmeppy’s efficiency. I’m running Storm King’s Thunder right now, which comes with loads of maps, and I can tell you that I’m not looking to recreate those maps in the Schmeppy grid which could take a long time. Certainly compared to a quick upload.
I’m in the current target market for Schmeppy, but I was disappointed when I couldn’t upload a map to use as a background. I really don’t want all of the crazy stuff that Roll20 can do, and I actually hope that adding this feature would not force you into appealing to the Virtual Tabletop audience.
Anyway TLDR please reprioritize! I would love this 