Jose:
Your question is hard to answer since you don't state the yield strength of the
steel used in your mast and you don't indicate how the 20 square feet of
antenna will be distributed along the mast. You also don't indicate if the
square footage of your antenna has been corrected for streamlining.
Assume a high quality mast similar to Array Solutions 2" (1/4"wall) 4130
Chrome Moly having a yield strength of 100,000 psi. They indicate the maximum
yield moment of that mast is 53689 inlbs.
Scenario #1 
If you assume a wind force of 50 psf (not unusual during a moderate hurricane)
and your 20 square feet (effective surface) of antenna is concentrated at the
top of the mast  then the bending moment (ignoring the effects of the wind on
the mast) will be 50 x 20 x L where L is the number of INCHES your mast sticks
out of the tower. In this example, L would need to be less than 54 INCHES.
This doesn't take into account the additional moment due to the effects of the
wind on the mast itself.
Scenario #2
If you think the above figures are too conservative... try this scenario...
40 psf wind, 20x.667 square feet of surface area (correction for streamlining).
This yields a wind force due to antenna of 533.6 lbs. Let it act over a
distance above the tower of 8 feet (96 inches). This yields a bending moment
of 51225 in lbs. Add the effects of the wind on the mast and you add another
142 inlbs. The total of 51367 inlb... is very close to the yield moment of
53689 inlb and provides for no safety factor.
I'm obviously not an engineer but I would damn scared to go more than three or
four feet (at the most) above the tower with 20 square feet of antenna in a
hurricaneprone area such as the one you're moving into. Raising your antenna
another 6 to 10 feet is not likely to do very much for your signal but it
certainly puts your antenna at much greater risk.
Tim, N4UM
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See: http://www.mscomputer.com for "Self Supporting Towers", "Wireless Weather
Stations", and lot's more. Call Toll Free, 18003339041 with any questions
and ask for Sherman, W2FLA.
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