Offer your thoughts or opinion on the input financial query or topic using your financial background.

What tax software automatically determines the best filing status, etc? 
Rob - I'm sorry your first visit here has been unpleasant.  What you are asking for is beyond the capability of most software. If you look at Fairmark.com, you find the standard deduction for married filing joint is $12,200 in 2012, and $12,400 in 2013. I offer this anecdote to share a 'deduction' story - The first year I did my MIL's taxes, I had to explain that she didn't   have enough deductions to itemize. Every year since, she hands me a   file full of paper substantiating medical deductions that don't exceed   7.5% of her income. In turn, I give her two folders back, one with the 5 or so documents I needed, and the rest labeled "trash". Fewer than 30% of filers itemize. And a good portion of those that do, have no question that's the right thing to do. e.g. my property tax is more than the $12K, so anything else I have that's a deduction adds right to the number.  It's really just those people who are at the edge that are likely frustrated. I wrote an article regarding Standard Deduction vs Itemizing, in which I describe a method of pulling in one's deductible expenses into Odd years, reducing the number in Even years, to allow a bi-annual itemization. If this is your situation, you'll find the concept interesting.  You also ask about filing status. Think on this for a minute. After pulling in our W2s (TurboTax imports the data right from ADP), I do the same for our stock info. The stock info, and all Schedule A deductions aren't assigned a name. So any effort to split them in search of savings by using Married Filing Separate, would first require splitting these up. TurboTax has a 'what-if' worksheet for this function, but when the 'marriage penalty' was lifted years ago, the change in status had no value. Items that phaseout over certain income levels are often lost to the separate filer anyway. When I got married, I found my real estate losses each year could not be taken, they accumulated until I either sold, or until our income dropped when the Mrs retired.  So, while is respect your desire for these magic dials within the software, I think it's fair to say they would provide little value to most people.  If this thread stays open, I'd be curious if anyone can cite an example where filing separately actually benefits the couple.