First of all, yea I did a search trying to find some of these answers without a lot of luck for some issues.
I am about to buy an '85 Hunter 23. It is the wing keel version without the swing. The present owner bought it in the slip that he still uses, however, he does have the original trailer. My plan is to use it as a trailer sailor. I need advice for the following type issues and any that I may not have foreseen. Pics would be great too. Any tips or tricks will be greatly appreciated.
--How to quickly disconnect the boom? Gooseneck, top lift, mainsheet rigging.
--How where to store the boom/sails?
--Should I remove the outboard each time or trailer in place?
I have found a book titled "The Complete Trailer Sailor." I will be looking through it as well.
I think that you will wind up getting a mooring for this boat because it's not going to be an easy boat to trailer sail. Years ago I tried getting the mast up on a Hunter 23 with my own Gin Pole and had a heck of a time but that may be a minor problem.
I just don't think that it's going to work out well for you.
Of course this is my own opinion and I could be wrong about that. I'll let you make the call.
As far as rigging the boat for faster and easier set up, I can help you on that.
You can use quick release shackles at both ends of your Main sheet and boom vang.
It may be possible to stow your boom inside your cabin and if so, you could keep your Mainsail on the boom with sail ties and a mainsail cover. I'm using this system on my boom:
http://www.cncphotoalbum.com/doityourself/sailties/sailties.htm
I'm not sure about how your topping lift is configured. My topping lift comes down from the top of the mast. If you have a similar set up, you could attach the topping lift to the back of the boom after the mast is up, and lead it right out of the cabin. It's like having a second pair of hands and you can stow it back in the cabin the same way when you get ready to break it down.
The boom's goose neck can have a rigging pin with a large cotter ring that is easy to put on, or you may be able to use a press button quick release pin. Don't use a "Fast Pin". Once you get your boom attached to the goose neck, you only need to get the sail slides in the mast and hook up you main halyard shackle which should have a quick release shackle also.
In order to put slack in your fore stay to take it off or put it on, you may be able to add an adjustable backstay unit. I'm not really sure about this. I had a Johnson Handy-Lock installed on my backstay years ago and it allows me to tighten all the rigging up without messing with my turnbuckles. Today I have a CDI Roller Furler and I'm able to connect it or disconnect it by using the Handy-Lock. I am using a press button quick release pin for the forestay also.
You'll need a Gin Pole for raising/lowering your mast, plus a mast crutch on your stern rail to hold the mast while you pin your tabernacle. I also have a mast crutch on my bow pulpit for trailering.
I've always left my outboard on the back of my boat when trailering but you can use your own judgment on this one.
My boat has a tip up rudder that I keep in the back of my truck. I mount it on the boat's transom and set the rudder blade hold-up pendant line, and tie off my tiller so that the rudder is centered, before I back down the ramp. It's easier than trying to mount the rudder after the boat is in the water.
I trailer sailed my 1986 O'Day 222 for eight years. I bought it new at the Boston Boat Show and it came with a complete roller trailer. Today I have a 23' Aluminum tandem bunk trailer for her and I have a club mooring.
Good luck!
Joe