"Mast Up" accessory
I use this:
http://catalinadirect.com/index.cfm?fuseaction=product.display&product_ID=636
It allows me to step the mast single-handedly, and provides excellent support while trailering. When I'm working on the boat, I can raise it up a notch or two to allow easy access through the cabin hatch. I switched out the black rubber roller for a non-marking yellow one. Only other thing I'd add to it is a push-button quick-release pin of the correct size. See link for style, but this one is not necessarily the correct size:
http://www.catalinadirect.com/index.cfm?fuseaction=product.display&product_ID=312&ParentCat=207
The addition of a couple of blocks and a line from the mast to the bow stem, or modification of the winch strap, would relieve you of physically lifting the mast if needed. But, as a desk-bound, over-50, weekend sailor, I have no difficulty lifting the mast by hand or controlling it, once the "Mast Up" is extended. Same goes for letting it down. An informed helper pulling on the forestay makes it simple.
As you'll read elsewhere in this forum, the biggest issues are the one or two shrouds which will insist upon becoming tangled as you raise the mast, along with the one or two 'T' bolts at the turnbuckles that will bind and bend. I like keeping the 'T' bolts lubed. Others use tubes around the lower hardware, or tape on the shrouds to keep things straight.
