Yes, it is really hard to maintain dirt paths in the winter time, to the point when I went through winter, even without time travel, I gave up. It just snows so frequently I had troubles keeping up. If you use all of your paths everyday it might be easier, though?
For colors, it's possible to mix colors to match dirt with an alternating checker pattern, but appearance of dirt color can vary based on the time of day or the weather. If you do make natural looking dirt, you'll either have to focus on a certain time of day/weather (like if you prefer a particular time of day for your dream town) or change it frequently.


Two on the top are during the morning (9am), one clear and one overcast, two on the bottom are during the same conditions, except at night (9pm).
There's also dealing with the sharp edges of a pattern, but flora can hide those, after all.