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SandS said..
yes you could try and sail around with a 90 percent jib but when the wind gets down to 10 or 12 knotts . you will be going no where.
and wishing you had the 135 percent heady on . you could run a furled headsail instead of changing sails . but the problem remains .
old guy single handed cranking on a big mast head headsail = big job ,almost too big !!
I know with my two speed st 40,s trimming the 135% heady on a 30 foot SV with some pressure in it ,is a big ask ,some people just cant do it .
you would need to put $15,000 worth of winches on her to even have a chance .
She wouldn't really go nowhere. Looking at J/35s, for example, ORC polars indicate that a boat with 105% overlap loses 2% speed compared to a similar J/35 with standard 150% overlap. Okay, different boat and most of that penalty would be upwind in light airs so maybe you lose 8% of your boatspeed when going upwind in 8 knots of breeze; you're still not too slow compared to many cruising boats.
My foretriangle's 20% smaller and no great drama. Okay, personally I much prefer a fractional rig with a 105% overlap but with a good modern sail Mark Twain would still be fun to sail for the right person. And from pics and memories, MT has four enormous winches on the cabin top; move two of them back to the wheel and you've got lots of grunt.
I know retired people with 40ft masthead rigged S&Ss who cruise the world's oceans quite happily, albeit in a boat with a proportionately smaller foretriangle but using the 150% (IIRC) as standard.