There shouldn’t be much difference, you might be able to leave the olive in place if it’ll fit through the frame. It really depends which end is the easier to extract from the frame – i.e. if there is there a small, awkward hole one end and larger hole with good access at the other end then go small to large.
If the routing is the same both sides then try the mech first and find out which way is easier then do the same with the calliper.
If the routing is loose in the frame and you have enough access then try to get some narrow pipe lagging (or similar) into the frame then run the cables through that, if you can’t do that you can use zipties tightened around the cables with the tails left in place to stop the cables rattling in the frame.