Thirty four years ago I started my saga, out here, with a 26hp Ford 1700 4WD. It was the perfect size for snow removal on my mile long gravel driveway and all other, smaller, chores around my 80 acres. Seven years ago - most all the smaller chores were completed except snow removal on the driveway - and I then knew I needed more weight and horsepower. I wish I could have obtained the same frame size with a 60hp engine and added weight - but that was/is not the case. So I moved up to my current Kubota
M6040 and can now easily complete the "larger/heavier" chores.
However - there are now those few times I wish I had the smaller tractor. The larger tractor, some times, requires that objects be moved so I can get to the work.
It appears that there will never quite be a perfect solution to all situations.