Shiva is a fractional with swept back spreaders and very stout rigging. She also has runners which support the headsail and a storm jib. We've seen no problem with sailing using only a head sail, but rarely do it. Sometimes for sailing 3/4 of a mile across the harbor to the fuel dock. Roll out, roll in. Simple.
More likely we sail with only the main if we use one sail and hoist it to motor to stabilize the boat. Getting the main up is more of an ordeal.. sail cover and manual hoisting... blah blah blah