Windshield Screws and Gap

[argus1]

There is a large gap between the bottom of my windshield and the top of the hull deck. The screws were loose. Tightening down the screws pulled the windshield down a little but did close the gap. Should I caulk the bottom of the windshield frame to seal the opening?

 

[R-and-R]

I hate to say it, but your best bet is probably gonna be to remove the windshield, repair the stripped screw holes and then re-bed the windshield.
Trying to squeeze caulk into the existing gap won't make for an appealing or lasting repair.
In its current condition, there is risk of water penetration into your top deck via those screw holes.

I'd also investigate why the windshield pulled away from the deck in the first place. If the deck is soft and pulling away, it may be pointing to a bigger problem.