Thanks everyone for your great replies!
As I understand your advice, a cutter rig with both foresails on furlers, a high cut yankee headsail and a self-tending staysail would be the best set-up for a singlehander.
I wonder if the boom furled mainsails would help - or if they are prone to jaming.
painkiller - I'm hoping to find a boat with a davit dinghy suspended aft to keep deck clutter to a minimum. The jib boom I'll have to deal with I suppose.
lenl1540 - nope - never sailed anything much bigger than 30 feet - and that was many years ago in university. I'm taking an ocean sailing and navigation course in the USVI in April, and will spend the next year learning as much as possible before even buying a boat.
sailorgirl - I'll look into the Crealock 37s also - don't know much about them. I like the tayanas because of the large fuel and water tank capacities, and the heavier displacement.
Klem - I've copied your post and filed it into my 'Sailing' folder. I wonder if a wind vane wouldn't be more reliable than an electronic autopilot? Maybe both, eh? Thanks for the great advice!
Thanks again everyone!