Trailering Tips
I used to trailer my O'Day 222, and there were a few things I picked up that might be helpful to you... You definitely want to have the mast in a cradle on the front and the back of the trailer - my trailer had a cradle that attached at the rudder pintles at the stern, and then I used a 2 x 4 creation at the bow pulpit, tied on securely, to keep the mast on the boat in the bumps. If you are going that far, you should also use a support at the middle, usually at the mast step (make something out of 2 x 4's that attaches at the pivot pins on the mast step).
For the shrouds and lines, I wanted to use duct tape to secure them - but that leaves an ugly mess that has to be dealt with later... so, I cut up black plastic trash bags into 4" wide strips, then wrapped them with the plastic, then put duct tape over the plastic - sticking problem solved.
At highway speeds, you'll find everything that is movable blowing like crazy in the wind, slamming around and nicking your gelcoat - so make sure everything is nailed down. A common problem is the companionway hatch - it is likely to get the wind under it and come flying off on the freeway - my boat was "hatch-less" from that very problem when I bought it. So, make sure you secure it front and back with those adjustable web belts, so that it can't possibly come off.
Everything in the boat also has to be secure, or you will have a huge mess when you arrive - so make sure everything is nailed down and low in the boat.
Some people use shrink wrap, even cooking spray, to keep the road tar, mud and bugs from adhering to the hull gel coat - they can be hard to get off.
Finally, try to drive slow - there are a lot of unusual stresses on a boat when you tow it, and you want her to be in good shape at the end of the trip.
It's all worth it, though, when launch the boat on a beautiful mountain lake. I always wanted to take my boat to Lake Tahoe - what a beautiful place to sail.
One final note - many inland lakes have banned two stroke engines - I suspect to keep the jet skiers off as much as to keep the water clean - so make sure that you're covered on that issue.
Have a great time - sounds like fun !