Filing a tax extension is not a big deal, not at all. It doesn't raise red flags at the IRS. It doesn't put you in the automatic "to be audited" file.
So why the heroic efforts to avoid filing a tax extension? I don't know. What I do know is outlined below; telling you what filing a tax extension will and will not do for you.
Filing An Extension Will Not Give You Extra Time To Pay
I can tell you that if you owe money, filing a tax extension will not give you extra time to pay. By the time you file the tax extension you still must have an accurate estimate of what you owe, and you must pay by April 15th. The tax extension simply provides you extra time to gather information and prepare a complete return - it does not provide you extra time to pay. In cases where you owe simply send in a payment along with your extension.
Filing An Extension Will Give You Extra Time To Prepare An Accurate Return
Although it doesn't buy you time to pay, if you need more time to gather information, filing a tax extension can be an invaluable tool and provide significant stress relief as it gives you an extra six months to prepare and file your tax return.
For more details, or to access the IRS form needed to file an extension, see the IRS page 7 Things About Getting More Time To File Your Tax Return.