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@Object
welcome to the forum, this appears to abe a refreshingly well though out post so I'll neglect my usual abuse and provide an answer for you.
I fully recommend a course of deep end therapy. Commit to one of the rides, don't worry about it. Eat plently of carbs for a few days before hand and just do the ride.
Most of them aren't manic in pace and to my knowledge we've only ever left 50*14 behind, though to be fair he was taken away in an ambulance).
The rides are always good times and riding in a group you tend not to notice the miles flying by as conversation saps up and emptyness that would be experienced doing it solo. If you don't want to throw yourself straight into one of the intercity rides then may I suggest one of the night rides. These are typically only 20ish miles. You'll likely realise by the end of those that you don't want to stop riding, this is the first sign that you can do longer distances.