First, Hunter always on the small boats the jib halyard designated as the red line. From the photos, I will comment on a few things.
First, I would take that shackle where it is attached on the mast step and move it backwards to the rear hole to help insure the jib halyard does not interfere with the furling jib. I would then leave it as pictured as to the routing.
Secondly, I would raise the sail on that CDI #2 furler further up. Then secure the base with a longer down haul if needed. This way, it gets the sail higher into the wind. Yes it does help. Secondly, it gets the jib higher away from the bow rail which helps to keep it from interfering with the jib.
as a former dealer who sold many 240's, this is the way I set up the boats for my customers and never once was there any issue.
As for the mast raising, insure the mast raise pole is seated all the way into the mast. Attach the jib halyard to the top loop at the other end of the pole. Raise it until the mast raise pole barely touches the top section of the hole in the mast and no more. Then attach the mainsheet with cam cleat down in the anchor locker. You have the mast side supports on the the 240 mast to keep it from going sideways when raising or lowering but on the 23.5, there are wires that have to be attached. Raise the mast and never put your hands on the middle of the mast raise pole or you will bend it and then the mast will fail or fall. When it is up and pinned to the hole on the rear of the chain plate, use your foot with shoe of course to release the cam cleat. Never use your hand or you could very well injure that hand as the line is under a lot of tension. In addition, if you have to leave the mast up partially during the raising or lowering to unstag lines or whatever, always hold onto that line in the event the cam cleat should fail or someone steps on the line releaseing it from the cam cleat. Bettery yet for security, tie if off .