I have an account with E-trade, but completely forgot to print the 1099, which shows $23. dividend received in 2008.

I used Turbo Tax, and I can use it to create an amended return, but I wonder if it's worth the trouble for such a small amount. If I don't file an amended return, will the IRS charge me a penalty when they match the 1099s that they received from E-Trade with what I reported on my return?

Even if the IRS does charge a penalty, it will only be a small percentage of the additional tax due. Since the additional tax isn't likely to be more than $5-$10 (depending on taxable income and how close to a tax table threshold you are), the penalty won't be more than $1.

Does filing an amended return increase the chances of being audited?

That's an old myth with just a bit of truth to it. Every amended return is examined by a person, but that's really just to confirm the contents of the amended return. Amending a return doesn't increase the odds of an audit on the other contents of the return. I submit at least a few amended returns every year and while I've had some correspondence about the specific amendments (I've always prevailed), I can't recall any of those returns ever being audited for anything else on the return.

Ira