1. How important is the ability to randomly generate vs just make a map manually?
I like the idea of randomly generating maps, but by the time I'm done toggling options I could have just drawn something rough, which has the added advantage of making me better at drawing maps, so it's a win-win.
2. Is the prettiness of the map really important? I've been wondering if maybe a more lightweight tool for pretty player maps would make sense. I think Worldographer is great for knowing where things are at and keep track of nations etc...
If I had the time to do hard-core worldbuilding, I would definitely hunt for a mapmaking tool I like. Getting something pretty takes time, and knowing me I will spend too much time on it.
3. Do you all like making battlemats? Traditionally I've used a big marker board for drawing battlegrounds. Not sure printing battlemats is worth the effort.
I printed maps for almost everything the last time I ran, but I work at a printer and was using existing maps. I would not do it otherwise.
4. Is your map making tool driven by your VTT? I've been thinking about maybe looking into a VTT (e.g. Foundry) as I have some old friends more distant now. We might have a nostalgia game for old times sake.
No, because I'm not involved in any VTT right now. If I were running something using a VTT, I would import existing maps or my own hand-drawn stuff. I think the hand-drawn stuff would make a VTT feel a little more like being at a table.
I've run a game once virtually,a nd used an existing map packet. I didn't care for it, because it was a lot of work to get to the map I wanted, move the bits around, etc.
5. Do you use a mapmaker for worlds, regions, small scale, dungeons, cities, towns?
I do not. I have toyed with several map-making softwares and sites over the years, but never landed on one to use extensively. Partly that's juts my awareness of my fiddly nature; I know that I will mess around with all the cool tools in a mapmaker indefinitely, so i avoid even starting on them.
So, generally, when I need a map I just Google image search "fantasy ziggurat map" or whatever, and just use whatever captures my imagination. Or just sketch something on an erasable grid map.