Not real sure of the value of your current tractor. Maybe $1500 or so to the right person? Brand new DYS 4500 is 2k right now. Good luck selling it, just have to find the right buyer.

My suggestion is buy a used better brand name with dealer support. Make as many calls as you can to local dealers as trade ins are about to start rolling in. You could try to go to a dealer and trade your current machine in. You'll get hosed on the price over selling it on your own, but it may be worth a shot.

I would have trouble going back to Sears if I were you. Local dealer of mine had an 06 Simplicity Prestige with 42 hours on it. Wanted $3500, I said let me sleep on it, called him the next day to buy and it was already gone. He turned it over in less than 24 hours. A deal like that with your trade in would get you to your price range and you'd get a beast of a tractor. Used JDs can be a great value as well. If you go the used route make sure you know what you are buying. You could jump on a great deal and wind up with no better performance than you have now. Do your homework before you buy, but be ready to make a quick decision.

Good luck to you.

There was one recently on Craiglist for sale so I emailed the seller. He said that he wanted $2000 for it. I haven't seen the post recently so I assume he got his price.

What do you plan to do with the "upgrade"? I'm no expert, but ran a CHEAP Sears model over a rough yard for a long time and it mowed just fine. If that is what you are doing, without problems, then I wouldn't change anything. If you want to do some serious work otherwise, then I would consider the advice in the forums to upgrade to a whole new class.

For the total cost of that sears mower, I never worried too much about bumps and bruises. A broken spindle was $30 and a couple hours in the garage. Pulled a cart just fine. NEVER would have considered subjecting it to real work though. Repairing/ replacing an engine or transmission is beyond me. A lot of guys on here seem to get a lot of work out of economical garden tractors, but seems to me you buy a little insurance for longevity and against headaches when you upgrade to a better class.

I had one to sell very similar to yours a couple of years ago and I asked $2,000 for it. I had a cart with it ($120 cost) but no weights like you have. It was bought at the asking price by the first person who saw it. Like swimjim said, look at used and you'll get a lot more for your money. You just have to know what you want and be ready to jump on a good deal.

I have had several craftsman tractors over the years and they have all given me great service. I'd think you could get 2k for it, at least around here you could.

A person can buy a brand new Craftsman DGS garden tractor for a couple hundred more. I would say $1500.00 at the very most. Just look at what they're getting on E-bay, not so much.