If I purchase the Business Inc package [ T2's ] for $249 for yrs 2018-2019, will I be able to upgrade to 2019-2020 at a lower $ when it becomes available ?
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The purchase price allows filing one return. Creating a return does not use the IKC. The IKC is used when the return is actual electronically filed or the CRA printed version is selected. Just preparing the return does not use the IKC until the return is filed. So, multiple returns can be created in the TurboTax module, but, an IKC is required for each return actually submitted to CRA.
There is not a discount for TurboTax repeat users. The purchase price includes filing one return and does not entitle a user to a discount in a future year/filing.