Just got back from two months in New Zealand where we bought a trailer boat for ease of storage etc. A couple of points stand out after use. The person who said they tow once a year and leave the boat rigged at dry storage is on to it. We actually rented a berth and left ours in the drink. Towing is no problem but you use your boat more the easier it is. You won''t take an hours evening cruise if you have to launch the boat.
As to launching there are two things i learned that realy helped with mast raising. Try to get the bow a little down hill to help raise the mast and keep it in place while you hook it up. Also make certain the boat is level side to side to prevent twist and lateral strain on the base and rig as it is raised.
Hope any of this is usefull.. Cheers, Garry