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Best Ride on Lawn Mower

^^^^^^
Buy once cry once.
A small diesel Kubota with belly mower would handle your needs plus you'll have the versatility only a tractor can offer for all the other chores/projects.
Here's my little workhorse pulling double duty as fallen tree/debris clean-up.
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Damn! That is bad ass man! I wish I had that kind of money in the budget right now
 
I use my 140 with a bagger attachment around the house and my 3025 with 6ft mower for the rest.
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$1500-$2000 Somewhere around there
In that range, your probably going to want to look at the big box store traditional lawn tractor style. You can pretty much take your pick, at which one and color you like best, most of them have pretty much the same transmission and engine and pretty much the same longevity in that price bracket. (Deere/Husky/Cub Cadet). With 3-5 acres your probably going to be buying mowers more often than you would like with what is available in that price range.

You may want to look at older used machines,

I run a 1025R for the heavy lifting and driveway maintenance and an X380 for the mowing and a little light garden cart dragging,....cheap they were not, but I don't expect to buy another machine for a long time, if ever. If I have to sell them because I move or don't need them, resale on Deere machines are some of the best in the business, so cost shrinks considerably. When I was shopping I was between Deere and Kubota, Deere was cheaper, with more features and attachments I wanted. I also liked Deere ergonomics better.
 

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Here are three that hit the spot price wise,

The main thing is to look at what transmission is in them, that is normally the fail point on mowers, engines are generally pretty reliable.

I have read that the Husky mowers use a stronger transmission on their big box mowers (Lowes etc) but I haven't confirmed that.

In the used market, one of the older craftsman LT mowers (grey ones not the new red) were tough mowers, I beat one to death for 5 years before I bought the Deere machines, and I bought it for $450. You can still find those in running shape, I think mine was a LT2000.

 
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