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I'm a little confused, you say you can't put a new olive on as it's crushed, and then say I don't need a new olive as you've swapped loads of brakes without putting a new olive in...
swmlon-
It's crushed onto the end of the hose, around the barb, if there's room to pull that through whatever it needs pulling through you can usually just reconnect it, if not then trim olive and barb off and fit new ones. If you're just buying plain replacement hose, make sure you either don't have a banjo fitting at the caliper, or you've got some kind of reusable banjo to go with it, Shimano ones come crimped to the hose and aren't removable from that hose.
snottyotter
It depends on the caliper, lever and routing, but as long as there is no bango on your caliper, then I imagine disconnecting and unbolting the caliper would be easier as you then won't have to remove the bar tape etc.
Unfortunately you can't just put a new olive on because it is crushed around the hose and barb. It may be possible to recover the barb but it is a lot of effort. Fortunately, you don't need a new olive. I've swapped loads of brakes without putting a new olive on, never had an issue with leaking.