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I recently bought the 31 HP model of the 66 inch XS, it was a left over from last year but it didn't have any hours on it. The machine is really nice but I have noticed that in the heavy growth in the spring if the grass is a little too long it could use a little more horsepower. I have had to slow down slightly several times so far this year because of the heavy growth, it's certainly not a deal breaker for me, but you may want to consider the larger motor.
we have 2 31/66. i cant see spending $1000 for four horsepower. i like the 31's that we have, the only time i've really had to back off is on the one with the mulching kit. but if money is not the question, then yeah you cannot really have too much power.
I bought 2 35hp 66 at the first of the year one has around 150 hours while the other is just over a hundred. There is no question I would buy the 35hp again. But I would never buy a 66 again. In fact today I called my dealer and ask them how much would 2 60 inch bare decks would cost me.
Allot of the debate between the two is based on how you would use it. Bagging or mulching the extra HP would warrent the increase or if your mowing long grass on slopes. If your just side discharging the extra is not all that big of a deal. I am not sure what the difference GPH in fuel is between the two. The only bad part about the big engines is that it sucks to feed them if you are not using that power on a regular basis.
AFD, why do you want to change the decks to a 60"? we demoed a 60" 31 and i was not impressed with it at all. i think the bigger deck balanced the mower out a little better, the 60" did not want to hold a hill at all compared to the 66. it does take some time getting used to the offset of the deck, but i think you may want to demo one with the smaller deck before you spend the money changing out the decks. just some food for thought.