When filing my LLC return with Turbo Tax Business, I had to purchase and download Wisconsin. I'm now filing my personal return with Turbo Tax Home & Business and will need to file with Wisconsin, as well as Illinois. Do I need to purchase and download Wisconsin again if I use the free state to download Illinois?
"If I use IL as my free state, do I need to repurchase WI?"
Yes. TurboTax Business State is a different product so you will need to purchase the individual state income tax version from within TurboTax Home & Business (if you use IL as your free state).