Slick trick...
I took an old paint roller frame, cut the 1/4" metal rod about an inch forward of the plastic handle, and cut a thread in the metal with a thread die (1/4-20 threads per inch). To this I threaded a 1/4" coupler (1/4" female threads on each end, found in the bolt department of a well-stocked hardware store). On the other end of the coupler I screwed in an eye bolt, 1/4" threads by about 3 inches long. Using about 20 inches of flexible chain, I inserted each of the end links into the eye bolt by prying apart the eye and then hammering it closed. To make things a little nicer (and softer on the rudder), my wife sewed a sleeve the length of the chain, using upholstery vinyl. I slipped the sleeve on the chain before attaching it to the eye bolt. I always carry on my boat an extendable paint roller handle (adjusts from about 3 feet to 6 feet). I use this handle with a bottom scrubbing brush, as well as with a floor broom to sweep the dock. For pulling up the rudder, I thread the old paint roller to the roller handle. I use the lines that are attached to the tiller to pull it up as far as I can do so comfortably. Then, I take my device, slip the chain over the outer end of the rudder, and very easily pull it to a vertical position. The length of the chain is a bit critical. You want it long enough to smoothly slip over the tapered end of the rudder, but not so long to allow it to slide up the full length of the rudder. I've used this for probably six or seven years (ever since the day I didn't get the tiller high enough and dragged it up the launch ramp, necessitating a fiberglass repair job) and it has worked beautifully. And I have the adjustable handle for a variety of other uses.