Shimano brakes really aren’t that difficult, I was scared of MTB hydraulic’s after lots of faff on cars over the years, and thought as everything is so much smaller it would be harder, but really, it’s not.
I would recommend bleeding them whenever you shorten though, I’ve just shortened 3 hoses, and replaced one, the shortened ones (following advice in link above, and several places online that suggest a bleed isn’t required) had small amounts of air in the system and benefited from a bleed, the replacement hose required a full bleed.
Buy the shimano bleeding tool – it’ll be £4 well spent, the mineral oil is expensive, but what ya gonna do?
With the replacement hose, I just cracked open the caliper bleed nipple and pumped the brakes until some fluid came through, much as you would on a car, then, when I thought the caliper and hose were more or less full of oil (with some air bubbles still coming out), nipped it up, and using the shimano bleed tool, bled the remaining air out of the top, easy as anything, and nice firm levers now.
On the newer style brakes that use the bleeding tool funnel on the lever end, it’s so easy, and cheap to do, I don’t know why you wouldn’t to be honest, it’s a non job, and just not worth skimping on!
Edit:
I would also add, you can re-use the barbs, but they are a bit of bitch to get out, the olives you can’t re-use.
Also, be careful as there are two types of barbs and hose, see this thread: http://singletrackworld.com/forum/topic/shimano-brake-hose-differences
Be careful cutting the hose also, they’re quite tough, would probably recommend a proper tool, after stabbing myself in the thumb, and one hose deforming with a craft knife.