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I've never really used escorts. The largest non-mission fleet I've ever had was about 6 terrapins for a trading run. I just don't like using escorts, and I rarely use fighters - I think that the ability to fight your way through any given situation without help would be important. Besides, what would happen if the pilot was skint, had no way of making money, and had an escort-requiring mission? Sure, its quite unlikely, but not impossible.
As for how to deal with 'superships', in the plug I'm working on, the REALLY big stuff is always in a mission - you never see the Drones until you're going toe-to-toe with one of their battlecruisers in a mission, for example.