If you purchase the correct tractor, you will not have to worry about resale value. And by correct tractor I mean the tractor that will serve you well for a decade or more. At 10 or 15 years old, the resale issues pretty much level out and you will get what you get based on brand, but at that age, a lot is based on functionality, condition and appearance. Most of us who buy tractors, and buy the correct tractor, keep them a long time. There are plenty of folks who trade them in every now and again, and they are probably the people who use their tractors to make a living, but for us city-turned-country types, or for us who have our own 3, 5 or even 20+ acre mini estates, we tend to keep tractors a while.