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I upgrade the watering can first. The charge-up to water larger areas is helpful and the increased capacity means less trips to a well or pond to fill it up. It's always the first copper tool, the first steel tool, and first gold tool I get. If you go heavy into sprinklers early though, you might not want to upgrade the watering can so quickly. I typically don't obtain the resources to really crank out quality sprinklers until late fall or winter of year 1.
I upgrade the pickaxe as I go down the mines. The lower you go in the mines the harder it is to break rocks. An upgraded pickaxe will break rocks in less hits saving you time and energy. I'll get the copper pickaxe by the time I hit the iron levels of the mine (40-80) and upgrade to the gold pickaxe around the time I hit the gold levels of the mine (80+).
I upgrade to the copper axe whenever I'm tired of the large stumps on the farm and decide they need to go. I'll get the steel axe when I feel I need to move the large logs on the farm. I'll upgrade to gold before the first winter because I tend to chop down all the trees around town in the winter and on my farm and an upgraded axe = less hits to chop a tree.
I don't use the hoe that much so it's never a priority to upgrade for me, but I usually get to at least copper level before 1st summer if possible and definitely by first fall. Once at copper I'll upgrade it whenever I have the materials and the money, but after everything else is upgraded. An upgraded hoe is still really useful but less so than the other tools. If you are going to plant huge numbers of crops in years 2+, you'll want to upgrade the hoe to at least gold.
I usually get all the tools upgraded to gold by the end of the 1st winter, or earlier. In my current game I have them all at gold versions and I'm in the last week of fall. Beyond that (to iridium) just depends on when I get access to iridium (and when I have the money).
If you don't mine that much, wait until winter on the pickaxe but it's really good if you happen to get some mushroom floors in spring or summer. If you find a mushroom floor, grab all the mushrooms as quickly as possible, then go back to the top and back down to the mushroom floor. It's pretty easy to make at least 30k a day and often twice that or more, which is very good for early game (IMO). I ignore everything but the mushrooms unless I see a valuable gem or gold ore is right in my path or something. But you don't always get mushroom floors. If you get one, it goes up one floor every day so, e.g., if it was floor 104 on day 1, it will be floor 103 on day 2. It will skip the 5s and 10s floors (e.g., 90, 95, 100, 105,110) and monster infested floors. The potential mushroom floors are 81-119.
You can tell a mushroom floor by the non-red lights. Usually there's a green light right by the floor entrance/exit. (I didn't learn about the lights until recently and it makes finding the floors much easier bc I don't waste time checking the whole floor. That way, I can scout all the possible mushroom floors in one day and know where they will be for the next couple of weeks.) There can be multiple mushroom floors. E.g., this spring I had two, then none this summer or fall, then three this winter. I try to go when the floor is near an elevator floor, e.g., 101, 106, 107, bc it takes less time. But I also consider the layout of some floors. E.g., the spiral ones are a pain and may not be worth it (but I would do it if it was my only mushroom floor).
It really depends on what you've prioritized in the game. E.g., if you get sprinklers early or if you use rain totems fairly often, you don't need a better watering can (or well). Same if you ignore crops (mostly) and focus on raising animals, foraging, or mining. But if you're focusing on farming (or, e.g, making ale or wine) and you don't have almost all your field covered by sprinklers (and don't use rain totems regularly), a better watering can is very helpful. You probably also want to upgrade your hoe.
If you don't mine much, a better pickaxe won't help you much. If you don't like foraging (and don't need the hardwood), there's not much point in a better axe (after maybe an upgrade) unless you plan to clear cut your farm in a short time. Even then, there's probably not much point in upgrading past a steel axe (unless you want to run a tree farm by regularly planting trees and harvesting wood). If you're tapping your trees and not cutting them down, an axe isn't that useful (except to get into the Secret Woods). If you regularly make sure that your entire field is planted at the end of a season so that the soil is left tilled and fertilized at the beginning of the next season, an upgraded hoe isn't as important. Unless you want to dig for snow yams and winter root (e.g., on the beach, by Robin's, by the railroad tracks) in the winter. Then you'll need to upgrade your hoe before winter starts.
I don't think there's a universal rule on what you should upgrade when but I do like upgrading everything to at least copper (1 upgrade). E.g., even though I rarely use a watering can, I do use it when I'm expanding my fields until I have enough cleared and planted so that a sprinker is worthwhile. That area is often pretty far from a water source and I'm lazy so having the copper watering can is nice. Same with a copper hoe. Plus, if you aren't focused on farming, you can drop off the hoe almost any time. If you rarely mine, you can drop off the pickaxe whenever it's convenient for you. Etc. So you may as well get all your tools at least a bit upgraded when you have the metal bars.
A better Pickaxe safes a lot time in the minds and makes your progress in the Skull Caverns much smoother. You also find more gems wich equals money.
The Axe because you need wood A LOT in this game and chopping down trees in 3-4 hits safes a lot of time and energy.
Upgrading the hoe saves a tiny bit of time but after you planted all the seeds you basically don't need it anymore (just for little gaps that happen on your field now and then).
I actually haven't upgraded the Watering Can at all because as soon as i can build sprinklers i build all the fields so that the sprinklers do all the work...
The Pickaxe lets you work deeper into the mine faster and with less energy expended. So, that's extremely useful for obtaining ore in general, and in specific, the materials for T2 sprinklers.
The Axe lets you clear more of the farm and lets you access the secret forest glade, for which you'll need ... a Steel Axe (as I recall).