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You are welcome. Hope It helped and did seem too ‘know-it-all-ey’. I think you should go for it, it will be fun! J
A lot of classes end up using spells which can help. With fifth edition anyhow.The older stuff has merit, and for sure revisit it whenever you want. Personally I think fifth ed removes a lot of hurdles that, 3.5 had (which I disliked, I won’t get into why. I’m kind of biased).
Regarding tech, you can have a dice roller make rolls for you in Discord, you just type in a short, very short, formula and it rolls the dice for you in the group chat. Please read up on roll 20 as you’ve had two recommendations. PMing and emailing can take time and it breaks the fourth wall say, if someone has to spend time checking their individual emails to get a file when you can just quickly send a map or pic up on discord people get instantly. Experiment with it, its free. You can do most of what you describe on Discord, more on roll 20 so don’t have MS Teams and email and Private Messages and google drives. It would be super clunky for the flow of a game especially if two hours isn’t enough time to get even a small bit of adventure done or your players attention span is as you describe in your two posts.
I’ve been doing Discord for a while with my group after they all went home from college. Its been good but I am moving more toward roll20 now. I would recommend if you are on FB to join the D&D 5th Edition Official page: lots of people on their sharing ideas and creativity and helpful too.
No I am not getting notifications for those but I haven’t started a thread in how long either, I do not come onto the forums much these days.