I'm in year 1 of winter and have never had more than about 40 squares of planting because I just can't water all that much and still level up other things along with gathering resources. Not having sprinklers or material for better than 4 tile sprinklers is keeping me super poor. I could sell some metals but then I'd have less materials to craft farming equipment and I still have a severe shortage of refined quartz. I can't make a recycler. I only have a handful of single heart npc's. I have no animal buildings because my money is going into better tools. I'm failing pretty badly. On the plus side I'm just one winter flower away from the greenhouse.
I don't think you're 'failing', maybe you just took a different path? Depending on how far you're on the mines, you could take notes on which levels ore spawns (if you really want it, you can ask/search of course, but I
think each area of the mine has a different ore). I didn't focus on tools until much later (IIRC golden tools pick/axe only at the end of winter), so you can probably do a good amount of things in a day.
For money, you could fish a lot in winter, but I have no idea what are the best places to get decent fish. You could also maybe make tons of kegs/jars so you can make better money from foraging (unfortunately those take coal, gold or iron which can be annoying).
For Refined Quartz, I didn't know you could smelt it until Winter, and that sort of pissed me off. The recycler thing too, since I had low fishing skill for a long time.
But here's my solution to refined quartz shortage just in case:
Crab pots. I have 10-12 of them in the small pond thing near the farm house, and I retrieve the 'produce' and put more bait every day. You can make at least 500g daily, and with 3 recyclers I made enough quarts for 56 Quality Sprinklers, so it's very much tried tested. Plus, you don't use coal, and I still have like 30 refined quartz. It's boring..but it works.
My playstyle is a bit weird because I was definitely poorer than most people since I hate watering crops.
My focus is always on automation/lower workload (and the only automation seems to be sprinklers), so I'm used to the terrible early game, and a sudden instant insane change to gameplay once I finish some idea/plan. I managed to play the first 3 seasons without going crazy, but as I said before, Winter with no waifu changed everything.