Get as much money as you can before the Egg Festival (13/Spring). Invest it in strawberry seeds. It's fine to plant them in the following day, you'll still get two harvests out of them.

First summer and fall cash crops are blueberries and cranberries respectively.

Silo before chicken coop. Otherwise you'll need to buy fodder. And you just need one silo, as long as there's space for more fodder on the feeding troughs. (If there isn't enough space, a cherry bomb does the trick.)

If you're going the CC route, with the standard bundles:

• check the travelling merchant every Friday and Sunday, for either red cabbages or their seeds. Otherwise you aren't completing it until Summer y2.
• the bus repair just needs money, and grants you access to the Desert that helps you to complete other bundles. Do it ASAP.
• another bundle to prioritise is the one that grants you the greenhouse. Plant all fruit trees there, around the arable plot (not in it).

Mushrooms vs. bats: mushrooms are a reliable source of income. Bats are really unreliable (specially in comparison with trees in the greenhouse), and they don't even help that much with the CC.