Try a mast raising/lowering rig
Most trailerable boats need at least two people (one to lift/pull and the other to steady it)to raise/lower the mast, but not everybody has help. Several systems have been "developed" to assist the singlehanded, either by steadying, lifting or a combination of both.Check the forum archives under "mast raising" and pick "H23" as the model. You will see a bunch of posts on the topic including information about several rigs. The ones by Ward Niffenegger or Mark Major are probably your best bet if lateral support is your main problem. My rig is simpler but is intended more for lifting than for lateral support. Good luck.PeterH23 "Raven"