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Welcome to THAC0 . . . with Advantage! We’re two friends that have been playing D&D a long time. While we both love lots of other RPGs, D&D likes to experiment with our emotions.
Take the rules. Learn them. Use them. Report on them. Get revisions. Repeat. It’s the playtesters life. Then there’s playing at 10th level and above which many many people do, right? No, they don’t? Ok, well, for those who do Ang and Jared get into it and some ideas for how to make it fun.
Fun Factoid
The AD&D adventure Throne of Bloodstone included pregenerated 100th level characters, with notes on running 100th level characters. Some of the advice for running adventures for 100th level characters in that adventure was to focus on endangering the PCs stuff, rather than endangering the PCs, for example, destroying the wizard’s spellbook. That’ll make you a popular DM!