Steps I would take:
1) try tightening up the windshield frame via the bolts on each side of the dash.
2) loosen the bolts that hold the door on to the hinge, pull the door into position, and re-tighten
3) and if it is still bad, loosen the bolts that hold the hinge to the tub up behind the front pillars. Again, adjust and tighten. These are a serious pain in the ass, especially on the driver's side
Do your catches line up correctly? If they do, then only the windshield should be adjusted.
I have had this problem since day 1 of owning a cruiser. After doing all these things, my passenger side door fits about like your picture looks. The driver's side door has twice as much gap, as well as gap below the hardtop.
Hope this helps, I will keep my eye on this to see if I learn anything too!
Mike