As is the case almost every year, tax day--April 15 in 2020--is apt to sneak up in a hurry. Whether you use tax-preparation software or outsource your tax prep to a CPA, here are some key strategies to ensure a smooth and worry-free tax season.

Strategy 1: Use a tax checklist or organizer.
Using some type of a tax checklist or organizer can help you avoid that paper chase and assemble all of the key documents you need in advance; completing your return is then a matter of filling in data. Tax checklists abound online.

If you outsource your tax preparation to an accountant, it's a good bet he or she sends you a tax organizer to work from, either paper or digital; such forms often come prepopulated with your tax data from the previous year. Comparing the current tax year's numbers to those of the year prior can be a handy way to track trends in your income, interest earned on your investments, and charitable giving, among other items.

Strategy 2: Determine if you'll be itemizing or taking the standard deduction.
A key next step in gearing up is to determine whether you'll be itemizing your deductions or taking the standard deduction.

If you employ a tax advisor to help with your tax return, he or she may have provided some guidance on this issue based on your 2018 return. If you do your taxes on your own, you can probably get a pretty clear view of whether you'll itemize or use the standard deduction by taking stock of the major deductible items. For 2019, your itemized deductions would need to be greater than $12,200 for single taxpayers and $24,400 for married couples filing jointly for itemizing to be worthwhile.

For most households, the biggest-ticket deductible items include state and local taxes (including property taxes), which are now capped at $10,000 per household; charitable deductions; home mortgage interest (note the changes in the rules that went into effect in 2018); and medical expenditures in excess of 10% of adjusted gross income.

Armed with information about whether you'll itemize or claim the standard deduction, you can then know whether you need to round up supporting documentation. If you're claiming the standard deduction, you won't need to bother, but if you're itemizing, you will.

If you're aiming to find documentation of your deductible expenses but can't track down all of the receipts you need, don't despair. The previous year's credit card statements, which you can retrieve online, can help you identify expenses you incurred over the past year; if your credit card company prepares an annual accounting of your expenditures organized by category, that can provide an invaluable tool to your deductible expenses. (I thought I had been carefully stashing away receipts and acknowledgments of my charitable donations, for example, but I found that my credit card company had documentation that I was missing.) Healthcare providers and pharmacies are also usually happy to prepare a year-end statement documenting your out-of-pocket outlays over the previous year.