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But yeah, either take it for an upgrade the day before it rains (check the weather channel on the TV), get it upgraded during winter when you don't need it (I haven't gotten to winter yet, I'm going on Harvest Moon logic here), or take it for upgrade on the 27th of the month (no point watering on the 28th as the plants will die on the 1st).
Winter is a great time to do it also like previously said unless you're like me and have tons of crops growing at a single time and need to upgrade it beforehand to make it less of a hassle.
It wont matter anyway because once you give him the watering can to upgrade or any tool for that matter you will wake up with it back due to the game thinking it disappeared (Lost & Found) so just use that then put it in a chest when you go get your upgraded can back.