On Jan 1st of each year start a folder labeled taxes (with the year.)
Everything that might be needed for taxes gets tossed in there. Receipts for charitable donations, stock transaction statements (especially if they’re RSUs and the reporting at the end of the year sucks – like my employers case.) etc.
In our case we have continuing education and licensing fees for my husband – toss the receipts for those in there. If there is charitable mileage – we toss records of that in the folder as they accrue.
When you pay your car registration – make note of the deductable amount (it’s not the full amount)… toss that in the folder.
Then, later, as the year wraps up – toss the transaction summer/year end reports from your brokerage accounts. As the 1099’s and W2s come in – toss those in as well.
It seems obvious – but I didn’t start doing this till about 10 years ago. Now I don’t have any issue with gathering the info. I just grab that folder.