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I guess that I'm asking a slightly different question. From a tactical battle map, MapTool is a very competent solution, with a bunch of other good options that vary mostly on your preferences. (Finding maps on the web is especially valuable which is why we built in searching the web for maps...

For building maps or whole adventures? How do you find it for actually playing? Do your players figure it out as well?

If you wan to shorten your learning curve for players then you should try out our VTT, Shard Tabletop. We usually find that players can get in create a character sheet and be playing in order 10 minutes.

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This thread has lots of discussion around the features and capabilities of different VTTs. What provides the best play experience so that you can spend more time playing games and less time focusing on the tool?

I have to admit that I really don't care for line of site for several reasons, including what you describe. With line of site the DM sort of loses control of the flow of the game with line of site constantly adjusting based on where tokens are placed. It also makes it hard to keep up with...

It is amazing to see the variety of opinions. In my experience when we play while the ad-hoc map works better on a mat, anything planned is a lot more work with a mat. While we completely agree that the in person experience is really where RPGs shine, we have moved to using a digital map even...

I am curious about your experiences doing the in between of a fully prepared campaign and just running something on the fly. Do you do much whipping up your own content preparing for a session? Is it just too much work to prep? Poor tools? Can't find good maps to download and integrate?

Making your own content either by whipping it up on the fly or preparing it before is always a challenge with maps. Tools for creating maps are hard to build and hard to use. It is amazing how hard it is to get something that is as quick as sketching on a mat, whiteboard or sheet of paper. I...

That can definitely be the case, but there are lots of in between cases. Moving around a dungeon means that you want to know what halls you are going down and where you have been, even though combat or other encounters are interspersed through the dungeon. Cities also can have a similar model...

There definitely is a balance to figure out between technology helping the game to play more smoothly and becoming a distraction. Fog/dynamic lighting along with token placement is a good example. There a lots of times where the locations of players is just not that important, moving around...

I have to agree. Much of what makes D&D interesting is creativity and personal interaction, which is very different than playing a video game. Both D&D and video games are fun to play but I am skeptical that D&D as a video game will ever be anything but a bad video game.

It sounds like you are similarly frustrated with existing tools. I have been playing D&D for too many years to admit to, and being in the software industry was equally frustrated with the state of existing tools. My equally long time friend and I, were frustrated and did start building our own...