What tax software should we use?

I have also used w2's from both California and New York with Turbo Tax with no problem at all. Ditto on the split residency and two state filings.

Um, I'm nearly positive http://www.taxcut.com/ does multi-state filings... but you have to pay for the extra state.

HR Block online lets you do 2 states.

Intuit's Turbo Tax software http://turbotax.intuit.com/support/kb/general-program-issues/entering-your-data/338.html. However, out of the box the TurboTax desktop software will only let you file one state return, it requires that you pay an additional fee to add support for an additional state return.

Did she live in Wisconsin the whole year while working in both WI and IL? If that's the case, the location of her job shouldn't affect the software you use. I previously used Turbo Tax and Taxcut while living in Maryland, but with me working in DC and husband in VA. I do have a vague memory of hitting a snag with the software questioning the different states, so if you're getting an error message then there may be an entry made wrong. But I did work it out and was able to file.

Actually, even better, is http://turbotax.intuit.com/support/kb/e-file/ef-rejections/1951.html which details the procedure to use if you worked or earned income outside the states where you live or if you were a resident in multiple states throughout the year.

When you buy TurboTax, you get the Federal return, plus one state. If you need to file in more states, you have to buy them separately. So if you and your S.O. wanted to use it, you could go first and do yours, making WI the first state (the included-with-the-purchase one), and then when she went to do hers, she'd need to buy IL in order to file there. Or, if you want to be cheap, just help her do her IL return by hand on paper. Looking at it just as the number of returns you'd be automating versus doing by hand, the included Federal component of TurboTax plus WI would get you 4 out of 5. My S.O. and I tend to have the same problem, and we typically just have TurboTax do the Federal returns and then whichever state the two of us have in common that year, and then if there are other state returns to do, we do them by hand. Typically they're quick — the Federal return is where most of your time gets spent (at least in my experience) since it involves more money and there are more complex deductions and rebates.

Just piling on to say this is totally doable in Turbo Tax (I use TT Deluxe). I am a legal resident and employee in TN, my husband lives and works in MA, and we file joint federal taxes using Turbo Tax. I've never had a problem with it handling W2s form different states. Luckily we only have to do one state tax (MA) b/c TN doesn't have a state income tax.

miss nax uses turbo tax with W2s from 5 different states (she's a touring artist) no problem. nax jr has income from Illinois and Ohio. ditto. Do you know anyone who does temp work as a tax consultant who could maybe walk you through it? You might want to start from scratch and not import last year's data, as there were maybe bugs.