Lots of things figure into whether or not a tractor starts hard or easy.
Battery power, as stated, is a big one. If you can't crank at a decent speed, it's never going to start.
A good battery tender will help with that in low temps.
Glow plugs can in time wear out, or get carboned up. As far as failure goes, one will probably start to fail first. Your sign for that is, since one cylinder is not hot, it won't have good combustion. It will run rough and chug, when cold starting. If you have tried a long glow plug cycle, and you still have incomplete combustion, your glow plug(s), may be the problem. You can find the cold cylinder with a non contact, infrared thermometer. That will give you a place to start checking.
Fuel quality is also important. If you buy your gas at the cheap gas, gas station, good luck. It's probably not that great.
See if you have a local place where the farmers all get their fuel. It's a good bet they sell a better grade of fuel. They don't want to deal with an angry farmer.
Basic maintenance, like a clean air filter is more important on these as they need to suck in much more air, than a gas engine.
And finally, operator technique is a factor. These are not like a modern car where anyone who can turn the key can fire it up. They do require you to roughly determine the combination of glow plug time, and throttle setting for your rig, at a given temperature. If you don't open the throttle when it's very cold, it's not going to start. And, you're going to have to go through some trial and error, to determine how much and when. I have never had to open mine more than 1/3 of the way to start it. So, I would not consider using the full throttle setting suggested in some manuals.