I can tell you what I have done about sails. My first racing jib was a North light 155 tri-radial made from a mylar laminate, great sail that was very fast. That sail lasted 3 years, then I realized we could carry the #1 up to about 18 knots of wind before the boat would be quicker with the #2. When the North got old and was no longer holding it's shape I purchased a UK Matrix string sail and had taffetta put on both sides for longevity, along with that I purchased a 140 from Doyle to be used as our #2. The #2 is Marblehead weave dacron which is a very economical cloth, which helped to offset the big dollars I spent on the Matrix. The Matrix with the taffetta is fairly heavy, but the shape is so good that our light air performance doesn't suffer too much. As far as the kites go a second halyard would be nice but we just aren't up to doing spinnaker peels just yet. We carry a 1.5oz reaching kite that doubles as our chicken kite when the wind is over 20. Then we have a .75oz runner that is close to 1100 sq ft. I also have a .5 oz kite just to play with. It really boils down to how much are you willing to spend and how good your crew is, because without the crew work all the money in the world wont help.

I am a big believer in Asymmetrical kites on a conventional pole, but it makes for a lot of string. Because I think the Cat 36 likes to run deep anyways, I use a 0.6 oz AirX symmetrical, which is oversized (code 6) and a pole that is 1' longer than J (so 15'3"). This gets the boat downwind in a hurry. I will be adding a 0.75oz kite that is a bit smaller as a 'chicken' chute and for hard spinnaker reaching.

When I get 2 kites, I will consider the halyard issue. In my opinion, unless your crew is pretty slick, you will do more harm than good by trying to peel spinnakers. I have done bow on a lot of big race boats and I still would not bother on the Catalina most of the time. So, I will probably stick with 2 genoa halyards and 1 spin halyard.

If you do insist on adding a kite halyard, the best bet would be to duplicate the existing one on the other side of the rig. I don't know if your mark 2 is the same configuration as my mk 1, but for me this would involve adding halyard exits at the top and bottom of the rig on the stbd side, plus removing the 'crane' on the front of the mast where the spinnaker halyard block is, and having 'wings' welded to it on either side to get the 2 halyards away from each other and away from the furler when cruising.

The attached pic shows the SST ring on the front of the crane, this is the part I would take off and have a couple more rings added to the sides of.

For upwind sails I am in the process of some upgrades, but it is a no-brainer that you need a decent 155% genoa and as much mainsail as you can put on the boat, plus a #3 jib around 100% depending on where you live.

I think the second spin halyard would be a real waste of time and money if you are just worried about it breaking. Most spinnakers will come to pieces before they will break the halyard.

I have the Harken furler with 2 luff grooves and removable drum. I have opted to have all my sails fit on the furler, as I am in a light air area and the #3 jib only comes out 2 or 3 times a year, and when it does I usually will need it all day anyways. If I was doing more racing, or longer distance (like 70+ miles) type of races, I would remove the drum so I could do sail changes. If I was doing a lot of that stuff I would probably have my sails made to fit in this configuration and pick up the extra sail area.

My mainsail is a 2 full, 2 partial batten affair, and I don't use any sort of 'containment device'. Frankly the mainsails on these boats are not very big. Even the main on the Melges 32 I sail on is much much bigger than this one. I would consider lazyjacks, but they are about 20 items down my 'want' list. I would never ever consider dutchman system, it has no place on a race boat and takes years off the life of your sail. It also makes the sail heavy and hurts light air performance, and finally, any real racers who step on your boat to crew will not be encouraged by it's presence. There is only room for one dutchman on my boat, and he will be holding the wheel!