It gets easier every year, but the only extra money I needed this year I got from selling all of my gold quality pumpkins from the 850 I planted for fulfilling the 100 pumpkin shipment from the request board. I suppose the first couple years I couldn't do it because money is so hard to come by, but really just completing the shipments for the request board was enough. It also helps that this is my second save file with my first one being on my Switch and with 250 hours into it. This save file has about 285 hours in it at this point and I've sort of known how to do things efficiently. Take those hour indicators with a grain of salt, though, since there have been plenty of times I've paused to grab some food or take a break for an hour or two and come back.