many tractors if you swap the rear wheels side for side so as to keep direction of treads on tires. you can either gain a couple inches or loose a couple inches of width on the rear end.
no brakes on front tires. only brakes on rear tires.
check your operators manual to find out what it suggests for counter balancing weight between front and rear of tractor.
always try to keep the FEL low to the ground to keep COG (center of gravity) low to the ground while moving.
i have backed up a hill in reverse a few times on rather ugly nasty slope of a hill/s with the TLB (tractor loader backhoe). so i could keep weight on the front tires. (backhoe weight and at that angle *ughs*)
if you have 4x4 / MFWD engage it, and shift to a lower range / lowest range gear option. and just take it slow. if need be the engine can help perform some braking possibly. by dropping the engine RPM's.
tire pressure lower pressure within tires can allow the tires to defalt / bulge per say on the ground allowing for more ground contact and in that more traction.
chains on tires can also allow for more traction.
if it is to wet it is to wet. no if's and's or but's. if you are putting ruts on level ground, the hill most likely just going to be the same. spring/fall around here are wet seasons and you just wait, and wait. till things dry up.
make sure your ROPS (roll over protection system) is in good working order (without finding out the hard way). were a hard hat. and make sure safety seat belt is properly adjusted. do not think you will push over a tractor or hold it up with your body, if it rolls, keep your hands, feet, head in side the ROPS/tractor.
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with above said.
How would I know if it's safe to try driving up it?
no one is gong to be able to answer that specific question. it is a judgment call at least for me if i was driver. if you do not fill you can do it, do not do it. if you do, do it, nice and slow. so if something happens you might be able to correct issue and keep on going. or slowly come to a stop and slowly get it back down the hill without rolling it.