Rob, try putting your H14T on the trailer stern 1st, that way your mast is already semi-raised, use your trap wires to keep forward pull on the mast so that when you have raised the mast vertical, it will stay there while you hop off and secure the forestay. You can use extra line with snap-hooks pulling forward to some part of your trailer but coming back to the jib blocks so that you can cleat off. I personally have always used really strong flat rubber bungee straps to keep forward tension on the trap wires, I muscle the mast vertical, check to make sure there is enough forward tension to hold the mast in place, grab the forestay and quickly hop off the forward beam keeping tension on the forestay as I move to secure it to the bridal wires. Has always worked well for me, I double up on the bungee straps for each trap wire, and always check the straps before each use. There are some who do not agree with bungee's but each to his own, works for me, is quick to attach-detach, have used them on all my cats, H14T, H16, P18, GCat 5.0 and P16, have not had an incident where the mast dropped yet, always mindful of enough forward tension to keep mast vertical, always mindful of keeping forward tension on forestay as I move forward to attach to bridal wires. I always sail solo.
http://www.thebeachcats.c…ictures/?g2_itemId=53380