I had similar problems raising the mast on my 20 footer by myself. I
tried "walking" it up as described, but had some hairy close calls. For
the past few years, I've been getting a little extra help from a device
that lets me raise the mast without climbing around. There is no jin
pole or baby stays. The mast raiser uses a spring to provide a helping
hand while you stand on the cabin top guiding the mast up with with
both hands free and no climbing around the boat required. The mast
raiser is pretensioned so that the weight of the mast is mostly
balanced before you start to lift. Then you raise the (almost)
weightless mast as fast or slow as you please entirely from the cabin
top. Since you have both hands on the mast (instead of pulling on a
tackle), there is really no danger losing control of the mast when
raising or lowering. It's easy and cheap to build and stows in a bag.

Mast Raiser Part 1: Concept
http://bbs.trailersailor.com/forums/...x.cgi/read/207

Mast Raiser Part 2: How to make it
http://bbs.trailersailor.com/forums/...x.cgi/read/214

Mast Raiser Part 3: How to work it:
http://bbs.trailersailor.com/forums/...x.cgi/read/218

Link to pictures that are no longer "archived" on TSBB:
http://tinyurl.com/4xj2q

Hope this helps, Paul