The Adobe CS6 Master Collection was something like $2500+ back at the final version. The Creative Cloud, which includes more software packages, more frequent incremental updates, some cloud storage and a few other trinkets and baubles goes for $50 a month. (They have been slamming my mailbox with a never-ending 40% off for the first-year "limited time" deal for the past six months.) I can install on both Mac and PC with same license.
In 50 months, I would break even - and probably have to pay a full version upgrade fee somewhere in there as well.
Microsoft Office 365 comes with their entire suite, though Word and Excel are all I need. It also comes with a terabyte of cloud storage and some surprisingly good iOS apps that take advantage of it. For the same $99 I would pay Dropbox for JUST the terabyte of storage.
But wait! There's more! (Billy Mays voice) That $99 gets me FIVE sets of the suite (and a terabyte of storage each) for my household.
I've messed around with LibreOffice, and other types of FOSS. They are OK, and probably the perfect solution for developing countries or non-profit organizations where every penny matters.
For me, I make my money doing actual work ON the computer, not messing WITH the computer. Futzing with second-tier "free" software is not without cost when I have to develop work-arounds for "close, but not quite" problems.
I've never understood how someone will sit in front of a $2800 iMac and tell me how much money they are saving by using GIMP to edit work that will be sold to clients. When they loose that client because of color-proofing issues on a 10,000 print run, will they have really saved money? This is picking up pennies and watching dollars blow by.
I don't feel gouged by either of these companies. It's a consumable business expense that "wears out" like tires on a taxicab, the phone system in the office, or fire insurance on the building I work at.