Software is a depreciable asset and is normally depreciated over a three year period for tax purposes. Off-the-shelf software qualifies for the Section 179 expense election which allows you to write off the entire amount in the year the software is purchased and placed in service.
The Creative Cloud subscription would be an ongoing business expense. If the cloud subscription costs more over the lenght of time that you normally upgrade the purchased version in, you have to decide if the extra cost is worth it – due to additional flexibility, features, etc. If there isn’t really much difference other than cash flow, it doesn’t make sense to spend an extra $100 to save an extra $35 in taxes.