I respect JeffH''s technical knowledge tremendously, but I often disagree with him

Jeff has a strong bias towards maximal performance in boats and tends to evaluate boats based on the kind of sailing he does most, which may not apply to everybody.
No question that mast roller
furling reduces performance, wears the sail, and could be dangerous if the sail jams in mid furl, however you could come up with equal arguments about broken halyards, batten''s that tear the sail of a traditionally hoisted main...etc.
One advantage for you in having a mast furled main is that they are very easy for a single person to furl and unfurl and steer the boat too. If your mate and children are not yet experienced sailors, then this would be a huge advantage for you.
If you are just beginning to gain experience yourself, it might help to have a sail that is less efficient, so that you don''t get caught in cases where you''re overpowered as easily.
I''ve sailed a mast
furling main around the BVI on several occassions and found it to be very easy to work with (though the boat wouldn''t point for crap). My girlfriend rarely got up from the deck and it was easy enough for me to manage all the sails myself (on a 40 foot boat). The only time I had trouble furling it was when I forgot to release the cam
cleat before cranking on the
winch.
I think if you are conservative and reef early, you shouldn''t have a problem, provided that you''ve done your homework and have read everything you can about this particular furling system.
As far as the other anxiety, I went through the same thing early this year when I bought my first boat. For me it was the difference between the boat being someone else''s maintenance responsibility and it being mine... did I bite off more than I could chew?
Now that I''ve had it for several months, I''m really begining to enjoy the maintenance and it''s all becoming part of the joy of owning a boat!
Good Luck!