Hello,
1. Do not pull the crown out at all. The crown-out position is only for setting the time. The crown-in position is for winding and wearing the watch.
2. Turn the crown until you feel firm resistance (i.e., until it stops with regular winding pressure) then stop applying winding pressure. Some say to back-wind the crown one or two turns to relieve some pressure on the mainspring, but this is optional. There is no established revolution number because it always depends on the existing tension (wind) in the mainspring at the time you wind the watch and the manner in which you wind the watch (the length of your winding stroke will result in more or less revolutions to fully wind the watch as compared to the length of others' winding strokes); however, if you wind the watch the same time each day using the same winding process, you will quickly be able to ascertain the normal range of revolutions it takes you to wind the watch.
3. Yes, wind it every day, preferably at the same time each day.
Hope your husband's health improves.
John