Resources & Important Links

The deadline to file your taxes is typically April 15th of each year. However, it may vary based on weekends, Federal holidays, or other circumstances.

• Filing an extension with all relevant taxing authorities will typically provide you with an additional six months to prepare and file your taxes, generally extending the due date to October 15th.
• It is important to note that an extension to file your return is not an extension to pay taxes due – meaning that, at the time of filing an extension, one will be expected to make an estimated payment with that extension to pay expected tax due. If this payment is not made, the taxpayer risks having the extension denied, and the eventual filing treated as late (despite an extension being filed).

The necessary documents to prepare a tax return will vary with an individual, however some common documents of relevance are:

• Forms W-2 reporting income from your employer(s)
• Forms 1099 reporting income from self-employment (1099-NEC), investments (1099-DIV, 1099-INT, or 1099-B), retirement accounts (1099-R), or other sources
• Accounting of any self-employed income and related expenses
• Form 1098 reporting mortgage interest statements
• Form 1095-A reporting Marketplace insurance premium and credit information
• Records of any estimated tax payments made
• Social Security numbers (or tax identification numbers) and dates of birth for yourself, spouse, and dependents

Charitable contributions and medical expenses will be relevant for folks who use and file Schedule A Itemized Deductions. These days, many fewer people would find Schedule A to be advantageous on their tax filing than had previously, so often this information is not relevant for a taxpayer. However, whether or not to itemize deductions is an individual consideration that cannot be adequately addressed in a general format. If you have significant medical costs, mortgage interest, or charitable contributions to report in a given year, it is best to provide that information and work with your tax preparer to determine whether it is relevant to your return.

Only if you like the idea of making an interest free loan to the government. The best outcome is to neither overpay nor underpay taxes. Obviously the bottom line is a moving target, but we want to come as close as possible. If you are one for whom tax refunds constitute an enforced savings plan, this can be adjusted. But generally, one may consider instead moving those funds to a different and more beneficial savings plan – one that keeps your money working for you, either in savings or in managing debt.

Like the answers to so many other questions – ‘It depends’. To avoid penalty, the taxpayer will want to prepay taxes that are the lower of last year’s tax bill or the current year projected tax bill. Depending on the relationship of last year’s relevant tax information compared to this year’s, there may or may not be a need to make those payments. Generally tax planning throughout the year will include determining what, if any, estimated payments may be appropriate.