I have a Cape Dory 25 and I raise and lower the mast single handed. It's easy.
Get a copy of "The Sailor's Sketchbook" by Bruce Bingham, Seven Seas Press
for full details. I paid $4.00 for it on Alibris.
That's one way.
The other is building a large A frame, and raising the mast by pushing up on an extension ladder, till you can hoist from the frame.
How much do you want for your Lightning?
This is a great boat in spite of the mast ordeal, if needed I can hire someone to build a hoist or hire a crew to put the mast up in the Spring . It has 3 mains 2 are very good and one is like new. One is cut for a storm main. It has 3 jibs all good to great. It has 2 spins and a canvas boom tent. It has a good trailer. I sailed it today in light air and it performed well. It is a 66 glass boat but has lived inside. It had new epoxy paint by a pro 5 years ago. It look more like a 1996 that 1966.
I was just shocked that it was such a PITA to put up a mast. I have been sailing over 35 years and had no idea a 19 ft, boat's mast was such task. Having said all that I think it is a keeper after all. Few people would want a boat this old at the price I was willing to pay but the former owner took care of it. I would sell it for 5 thousand.