there are two types of brake hose (and associated fittings) - does it matter if the lever end requires one type and the caliper another?
No, the XT M785 and related systems used a Banjo at the caliper and the standard olive etc at the lever.
I never had leakage from the banjo but many did.
Also Shimano's "new" easy fit system appears to be a case of the pipe being pre-fitted with a barb, and the olive sitting waiting for the pip to pass onto it and the bolt to be tightened...