Being a transplant to the flatlands of the eastern seaboard, our coldest winter day is a warm spring morning by northern Idaho standards.
Tractor motors are usually heavy, and it takes a LOT of heat to warm one up. Even on warm days, it takes longer than you might assume for the oil to make it up and around most engines. Warming the oil should/may help reduce that time it takes for the oil to first get around. BUT, it's going to be stone cold when it gets back to the pan. Water jacket heating helps a bit with that, but I've noticed they are better for frequently used machinery (at least daily) if it's being used without heating the oil. So, if the goal is to reduce the overall punishment to the machine, you first should sign-up to letting the tractor warm-up for at least the time it takes for a cup of coffee and two smokes after it starts regardless of whatever warming (if any) you choose.
I really hope this is stating the obvious, but over the last couple decades I've noticed a tendency of people to be in gear and rolling before the starter quits spinning.