I think it would work for you..... I, quite frankly, can't imagine doing it regularly without a winch. I've done it without the winch solo and it is no fun. (A mechanical friend is redesigning my set-up with a 12 volt battery and winch mounted on the back end of the trailer and a line running to a block on the mast support post on the front of the trailer and then up to another block and up to the forestay. He thinks with a remote controlled winch I could stand on the ground with the mast on my shoulder and with one hand control the electric winch and solo winch it up. Sounds kinda Rube Goldberg to me.....)

I just re-mounted my winch down low on the mast support post on my trailer and attached a block up high so I can increase the angle of lift. I'll shoot you a picture if you think it would help you. I'll also shoot you a copy of my pre-flight plan if that interests you too. Yours will probably be different than mine but it would give you a starting spot perhaps...
Greg

The nice part about being a pessimist is that you are constantly being either proven right or pleasantly surprised. - George Will
"It's not that liberals aren't smart, it's just that so much of what they know isn't so" -Ronald Reagan