I know the rules technically say 'play game' is the start of the run but I'm assuming if we want to start with 'endless' instead that'd be fine, too? Since either game option allows for achievement earning progress to be made.

The all achievements category sounds like it could be fun but I'd personally want to get the challenge mode related stuff out of the way sooner rather than later.

Yes, that’s a good catch. Will update the rules in consideration.