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How tech savvy are we talking? I can troubleshoot the usual stuff on my pc, by googling. But I’m not a sysadmin and have 0 knowledge about how to set up or maintain a server.
My group has been looking at TTRPGs for a while now. We used Owlbear Rodeo for one campaign, and started our current one on Roll20 without premium, but… It’s so unintuitive. An honest to goodness UI/UX nightmare. I can see the logic behind some of the choices but it’s so uncomfortable to use. We want something with a bit more functionality (character sheets and dice rolling at least, dynamic fog of war being a personal bonus as a DM).
Depends on what you want out of it, the level if automation etc.
Installing a system ruleset, adding a few modules and other things on that level is easy. If you can use an app store you are set. Writing custom things I have no clue about.
Finally using it. I’ve found it smoother than roll20 and fantasy grounds. Just not having to deal with roll20’s technical baggare is truly awesome.
In the end my impression is that on a technical level it is much easier to handle. Less figuring out how not to have the platform work against you and actually work with it.
You, depending on your ISP, may have troubles self hosting. There is the biggest technical hurdle.
Are you savvy enough to search the internet for a guide on how to do something technical, evaluate if the guide you find is right for your situation, and then follow that guide to do the thing? That’s basically how I set it up for myself. You don’t need to understand the deeper workings of stuff. If you’ve ever modded a video game before or troubleshot a software issue, you’re probably savvy enough.
FVTT does all of the things you mentioned here out of the box. No need for tinkering.