Dave: Under good conditions, example sandy loams, it should handle 4, but heavy ground could take it back to 3 bottom. Not sure I'd want any larger than 3 bottom in a trip lift. That traction wheel sliding on 3, 4 and 5 bottom plows is what drove folks to hydraulic lift, and the bigger they were, the wrose the problem.
 
a 3-18 oliver is a nice plow behind the 9. if you want to add hydraulics, check at the farm sales for an old char-lynn pto mount hydraulic pump. its an all in one unit that slides in to the pto shaft, and gives you two way hydraulics. heres a pics of one on my 9, it is just below the blue tool box, not quite the size of a 5 gallon pail, but they work real good. lever to the right operates the hydraulics
<a href="http://s121.photobucket.com/albums/o234/glennster_01/?action=view&current=DSCF1628.jpg" target="_blank">
DSCF1628.jpg" border="0" alt="Photobucket
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I'm torn between my usual advice of not trying to work these old tractors to hard to preserve them, and the fact that even three 16" bottoms will look silly behind a big ol' W9.

If the tires are loaded, I'll say four 14" bottoms. Otherwise three 16" (or even 14") bottoms.

Occasionally you'll see an old IH #16 in a 4-bottom for sale.

Agree with Hugh on the trip lift, though there are measures you can take. That lift wheel should have the best traction-type tire you can find. Minimum of an old snow tire off a truck, or better yet a standard lug-type installed backwards. If the going is particularly slippery, I've even heard of them using tire chains on the lift wheel.
 

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