Go look at some other boats.
Dave, there should be plenty of catalina 27's in your marina. On my dock alone there are 6. Anyway, cruise around and look at them. I guarantee you will see many different set ups.The attached picture shows my boat's economy set up, I like the jam cleats because they are cheap,and easy to release in an emergency. There is a stacked, 4 sheave organizer to lead the lines around the hatch. The two bottom lines in the picture are the main and spinnaker halyards. I use the winch for these. The other two are the vang and cunningham which don't require the winch. The port side is similarly set up and at this point I have only two jib halyards implemented. Many sailors run their reefing lines aft also, but where I sail it's rarely necessary to reef.For my spinnaker pole I have been using the spare jib halyard, but I plan to install a dedicated topping lift one day. This I will cleat at the mast, and let the crew deal with it. The foreguy (that's the pole downhaul) is directed along the base of the stanchions and cleated on the cockpit coaming. I have this set up to also serve as a "tackline" for the cruising spinnaker that doesn't use a pole.Sorry, no picture for the spinnaker set up. I'll see if I have one somewhere and post it.One more thing, your current main halyard might not be long enough to reach back to the cockpit. If you buy a new one, 80 ft will be enough. Check the archives for halyard options. I can say this, if you want to replace with wire to rope, you can save money by going to Defender.com. 40x40 1/8"wire 3/8"rope will do it.