What will help you is a 'swing up or hinged tabernacle' at the base of the mast:
This is essentially a 'hinge' thats bolted to the coachroof top and to which you 'bolt' the mast base/butt before raising. The 'hinge' then provides more 'stability' during the raising process.
Also do websearch for 'gin pole' an 'arm' thats attached perpendicular to the mast during the raising process which mathematically lowers the amount of force needed on the 'forestay' and the mast when raising/lowering.
The use a of 'mast hinged-tabernacle' and a 'gin pole' will make mast raising lowering easier and safer ... and 'quicker' too.
Try this website for 'trailer sailors' for more detailed info: Trailer Sailors - SailboatOwners.com