Since he said he didn't want to be fixing before use each time, I wouldn't suggest a well used auction tractor.
An individual might have a good used one, but likely want what he owes on it and with 0 down and low interest, likely it is about the same or more than a new tractor. The only advantage of used (1-2 years old) is that you can get them with the lower EPA requirements so not so much BS on the engine to wonk out and especially no DEF to add and wait for regen cycle sometimes like larger tier IV tractors + many of the new diesel require an ECU computer just like our cars which is another $1000+ item to break.
I would look for a 2013 or 2014 hold over (NEW) and get the best financing available and highest HP that I could get. LS makes good tractors and they are cheaper than the other brands and have lots of standard features that other brands charge at least an arm for and some times a leg too boot.
With regard to FEL and 4 WD, if you have never used those, then you really don't know what you are missing. 5 years ago I would have argued that FEL was not needed but I did think that I needed 4WD and am super glad that I got it as it has gotten me out of some muddy situations many times.
You just don't realize how handy a FEL is if you never used one (like me before I bought my first tractor with one). I use it for moving dirt to fill in holes, digging out my dried up ponds, hauling material like wood, sand, rock, timbers etc. cause it sure beats a wheel barrow. MY wheelbarrow hasn't been moved in 5 years except to move it out of my way once to a better storage location.
I wouldn't recommend a FEL without 4WD due to lack of traction when the FEL bucket is loaded.
Lastly, except for PTO related activities, a 4WD with 20 HP will outperform a 30 HP 2 WD tractor due to SOO much better traction.
