I'm looking for software to use for mapping, but I would like for it to be cross-platform. Specifically, some combination of Windows, OSX (Mac) and iOS (iPad). I have all three and they get used in different circumstances, but when I'm away from home I'm carrying Apple stuff exclusively. I'm an IT professional and I'm familiar with things like virtualization and I am aware I can dual boot the mac or run VMs on it (and, in fact, I do so) as well as other methods of running Windows software on OSX. What I'm really looking for is native software. I'm perfectly willing to buy software. It doesn't have to be free.

Some background: I'm not an artist. My mother was, but I'm not. On a computer, I have had the most success with a vector based program and even then I won't win any awards. Also, I haven't done any mapping in years. In the 90s, I was drawing some truly awful maps with Deluxe Paint on my PC. Around 98 or so, I switched to Campaign Cartographer and things improved but circumstances were such that I pretty much stopped playing with maps sometime around 2004. Now, I'm looking to do some maps again for an RPG campaign I want to run. I was reasonably happy with CC back in the early 2000s, but it isn't cross-platform and they don't seem to have any intention of changing that. Unlike 12 years ago, I am using several platforms now, so I'm trying to see what else might be out there.

I suspect the problem will be the iPad. I don't see much variety there at all.

Thanks for any advice.