It cost me money to learn two things in the last 3 years:
4WD is essential in Kentucky Hill Country.
Tractors need size, footprint, and HP to do some of the things a farm requires.
I started with a JD 5055 D, open cab, 2WD. I traded it for a JD 5083E, 4WD, Enclosed cab in the first year. Lost about $2,000 by that mistake. But I am thankful I was not too hardheaded to realize I made a mistake. My pastures are steep. My bushhog weighs 1100 pounds and is only a 6 foot heavy duty rotary cutter but it was causing me to break traction often enough that I was going to get killed. The 5083 E with 4WD has probably saved my life. I manhandle my bushhog now.
I can say this. I have owned dozers and operated a skid steer. I love a skid steer but the FEL on my tractor with 4WD is very impressive compared to a skid steer. The skid steer does offer advantages in close quarters.