Help with wargames on Roll20

I've started getting into Frostgrave and the other wargame titles by Joseph McCullough but my friend and I are too far away to play in person. I know Tabletop Simulator exists but we've been using this site for years and its worked well up to this point. Has anyone had any success playing squad based wargames that have 3d terrain on Roll20? How did you label terrain's height, line of sight issues, etc...

LoS can be easily handled with dynamic lighting, however I ran into the same issue as you mention when it comes to handling height differences in terrain on a top-down view. It would be really nice if there was a way to represent that difference in height by stacking layers. I understand that it might get complicated to allow us to do like say 100 layers, but could we get like 20? 50 feet up or down to represent different levels in height in 5' increments. Would make it possible to do "3d" combat for underwater and aerial battles as well...

It might be possible in some cases to simulate height differences with the "One-Way Dynamic Lighting" API script(available for Pro subscribers). Unfortunately it's doesn't seem to be a practical solution for your war-gaming, as it the trick the API uses results in all players sharing vision for the one-way DL segments. On a positive note I tried to use the script, but didn't figure out how to make it work. I don't really GM on Roll20, so not too familiar with DL or API scripts, but someone who knows this stuff better might figure out something useful from this. The script's author had an interesting comment about the future of One-Way Dynamic Lighting(emphasis mine): There are some paradigms I've considered when implementing this script that would allow each character to have their own perspective of the dynamic lighting . Unfortunately, this would only be possible if it were implemented in Roll20's dynamic lighting system itself using some WebGL magic involving stencil buffers and lighting polygon unions. A while ago, I presented an algorithm for implementing one-way dynamic lighting in the dynamic lighting system .  If it's compatible with their current system, maybe the Roll20 developers can make use of it. For the time being though, I hope that this humble script will suffice for everyone's one-way dynamic lighting needs. Beyond just improving performance and all the other things, the fact that Roll20 is working on recreating DL and FoW in WebGL will mean more features will be possible to implement, and give more options for API as well.

What kind of maps are you using?  It was a long time ago, and was only for a couple sessions, but I think I remember Robotech (or maybe just the DM of that game) using some sort of hex map system.  You could use a combination of symbols and colors to give terrain/obstacle type and elevation.  You would probably end up with something that looked like the color bands and blobs of a topographical map with symbols for trees, buildings, cliffs, etc. layered over that.

Frostgrave is usually measured in inches on any old battlemap. When we were testing it out yesterday we just said every roof of a house is three inches tall, walls were two, and every other obstacle was 1. So a 1 inch tall figure could shoot over cover if he was at least on a wall and the enemy was further than an inch from the cover in question. It didn't allow much variation but it kind've worked. I might add markers for difficult terrain and that sort of thing. Also sloped rooves, stairs, and gently sloped hills were all pretty difficult to simulate. If anyone wants to try it out send me a PM me and we can set up a time to play.

At least for tokens, elevation can also be indicated by using status markers. When you hover over a status marker, type a number from 0-9. It will be superimposed over the marker. You can use multiple markers if you need extra digits: