I am as daring a person as the next, and maybe more foolhardy, but I would not trust a line run any higher than the hounds. I recently went up the mast on a larger mast and I realized how much one depends on the correct tailing at the winch. By all means use safety at every place you can, and a 2nd line at the minimum.
On the other hand, since I don't have a roller furler, I can put my mast down and back up again in just a few minutes....why can't you?