Hi, I have a Macgregor 26S. She came with her own mastraising system (ginpole). It can easily be managed by a half portion like myself. Always cracks me up when I'm at the marina and have to winch the mast up or down. A mast hanging in the air at 45 degrees seems to have a frightful attraction to other sailors who quickly run to the rescue, just to notice that everything is perfectly ok
Whatever boat you end up with, a forestay lever helps to get the last free centimeters close enough that you can pin the stay in place IMHO.