The winch on the mast is an easy move. The genoa furler, figure a boat unit or two for the furler, IIRC one has to remove the forestay to put one one. Along with about $7-8 per lin ft of your jib luff to put on luff tape vs the hanked on jibs. Or about $200-300 for a jib on this boat.
Life lines, again, are very doable yourself with either no wire or Amsteel rope/line. A repair or two to the keel for a boat that age, frankly, while not normal, I would still put it in the "not suprised" catagory. She does look well loved overall, and would be a good boat for daysailing, weekending, occasional week long depending upon how much room you need.
Are the cracks around the lifeline stanchins? or near something equal? If so, then it may not be anything major if in the gelcoat itself. If it goes deep, then it is an issue.
She drives me boat,
I drives me dinghy!