Excel: IF statement with date range plus more

I'm learning to use formulas in excel I need your help with this IF statement.

https://drive.google.com/file/d/100EMdVteAgJO-ilDz8QNgtFEWWrBtqKb/view?usp=sharing

So when you see the sheet, I want to type in the data on the "Item" sheet and have it automatically added into the "Year" sheet. I want it so it looks up the date, category then adds the cost into its category on the "Year" sheet.

I played around with some IF(AND) formulas but nothing seemed to work.

Can anyone help with the formula?

Thank you