This is the way

I've never had an issue home brewing stuff that's close to my nondigital content. Or even using it. Just can't publish it for people outside of my campaign. But within the campaign it's anything goes.

Anyways, I'm in a funny pickle because if I buy everything on roll20 then I'm paying WotC again. If I just move my group over to there without buying... I have to homebrew every class feature for them, which is a nightmare.

So I'm just going to use ddb for as long as I can until they make me not want to anymore.

My players would have nowhere to make character sheets. They like the digital "do it for me" style.

I do. I'm waiting for the service to change in a way that impacts me negatively

The Nazi occult history/tropes are so prevalent that a WW2 setting is easy to make semi-historical sounding.

Source: I did a WW2 twoshot

Yeah, talk about cursed items

Your first two sentences sum up my anxiety about getting my group to switch. A grand total of one player would be fine in the new system. They're married to the player that already struggles with 5e, so in theory there could be additional office hours there to explain. But if they can't explain 5e in a way that sticks...

Wizards love tests but I don't know about the other casters