Hey. I was in nearly the same boat (literally) 4 years ago, when I purchased my first Hobie 14. I will attempt to answer most of your questions; you may also want to look at the H14 forum on
www.hobiecat.com 1) Standing rigging: After a 4 hour tow back from the middle of Lake Erie due to a broken shroud, I highly suggest that you spend the money to buy a new forestay($21), bridle wires(2x$16), and shrouds(2x$23). I have purchased them through
www.saltydogmarine.com and they provide about a 10% discount if you buy a complete set.
2) Trailer: They seem to show up on ebay and sell for around $200 in junked-out condition (needs new rims/tires, bearings, lights, wiring). Any catamaran trailer should work, because you can easily adjust the width of the rollers.
3) Tacking: The uni-rig setup and the fact that it is a catamaran makes the 14 a difficult/slow boat to tack. As for the turbo rig, here are my thoughts from a previous post:
Here is a link to a previous post that discusses the 14 Turbo's tendency to pitch pole:
http://www.hobiecat.com/community/viewtopic.php?t=1016 My 14 began as a turbo, but currently she is the standard, race legal rig. I am quite biased against the jib, because at the Shore where I grew up there are about 12 H14's all without the jib. The old time sailors that have owned the 14's since new in the 70s/80s saw the turbo as a marketing gimic. Say goodbye to ½ of the tramp as the blocks for the jib are not located on the front crossbar as with the 16 but squarely in the midsection of the trampoline.
4) Trap: I cannot tell from the picture if your boat has a dolphin striker, but you must add one if you would like to setup the boat with the trapeze setup. They sell these at murrays.com
And that is about all I have to add. You can have a ton of fun on the 14 with very little money. Keep in mind that if you add expensive upgrades (turbo kit), you will not see a return on your investment when you decide to upgrade boats. The 14's (turbo or not) do not sell for nearly the amount that the 16's do.