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As a mower I think you'll find it to be everything you would want and more. As a tractor it may fall a little shy of what the older units can do. I have a Conquest that is my turn key mower. It has a weaker transmission than the Landlord you're looking at and I plow snow with it, no problem. When you see the sub-frame that is used to mount the plow it will give you an idea of the strength and structure that has been removed over time. I'm also restoring a 3416 Sovereign that will be my worker as you cannot beat the older units for strength, durability and most of all for me, a plethora of cheap attachments. The tiller setup on a Conquest will set you back $1800 and they never show up used. On a Sovereign they show up for $200-$400 all the time. The only weakness for me is in the bagging/fall cleanup. The turbo blower and bagger setup on my Conquest gets pine needles, leaves, and grass clippings; the older units didn't really concern themselves with bagging and if that's important to you it will be more difficult to accomplish with the older machines.
Seeing that your looking to do what I'm doing in terms of a mowing machine and a working machine, I don't think you'll go wrong with the Landlord as a mower. Foot control hydro is great for mowing and the K71 will handle mowing on a hill with no issues.
 

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The diff lock is a manual pedal. If you look at the second picture it would be pressed by your left heel.
It should also have a limited slip that prevents only one wheel from spinning. I rarely need the diff lock out side of plowing or hauling out in the leaves. That said, when I need it I'm VERY glad to have it.
A Wheel Horse is a fine machine, but asking in the Simplicity forum is going to skew the results. Nothing matches the floating deck for the quality of the cut that the Simplicity is going to bring. If your going to mow with it 98% of the time, then 98% of the time it will out perform a Wheel Horse.
 

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The Massey 2716 is the twin to my Conquest, and in my neck of the woods that is a really good deal. If it were me I would grab the Massey and not look back, but the Landlord is a beefier machine.
1st and foremost walk away if you feel you should. I've walked from some deals in hindsight but I rather regret missing a deal than being taken to the cleaners. (A 4x4 Conquest with a 54" mower and a plow for $2000 comes to mind.)
Things I check; steering play and where in the linkage it is if it has any. (The steering gear is $60-80, a drag link end is $5.) This includes the axle bushing. I know they are a weak point on the Massey, but I also know it's a $30 fix. Listen to the transmission as you drive it and make sure it doesn't sound like it's grinding anything. Check the locking diff that it works (steady pressure on the pedal making a turn and it will push all the way down and it should now fight you to go straight. The Massey, like my Conquest should just push you in a straight line regardless of where the front wheels are pointing.
Listen to the PTO clutch engage and the deck for metal on metal sounds. Check the blade spindles for side to side play. I believe the common agreement is that 1000 hours roughly equates to 100,000 miles on a car, use that to judge condition and negotiation. I also believe that Briggs Vanguards (in both units) are rated for 2000 hours of life before a rebuild, part of why they cost what they do.
I don't think you would go wrong with either machine really. I KNOW that the Massey will do what you need and the Landlord is beefier than that.
 

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They are both Simplicities, just one is badged a Massey. It will be a K66L which has traction control and a locking diff. The Landlord is a beefier machine with hydro lift and steering but more hours on the clock. While the Massey doesn't have the hydro lift or steering it also means they won't break on you. If you search on my name you can view my postings on my Conquest. It is the exact machine the Massey is, 16HP, K66L, 44" Deck. I bought it from a dealer in WI and had it shipped, I've done a bunch of service on it and posted most of it up here with pictures.
 
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