I'm not sure how I would feel about a subscription OS. If I was still working, I'd probably suck it up and pay so that I could be 100% certain of being able to run any Win based programs I might need to telecommute with. Now that I'm a bum, I'm pretty certain I'd just either live with the last non-subscription Win OS version as long as I could, or switch to Linux as my main OS (run it in a VM now).
I already am sure I won't do subscription MS Office. Again, it might be different if I was still working, but I've been getting along fine with Office 2010 for years, and could probably get along fine with Office 2003. Though I'd likely just switch to Open Office, which has gotten VERY compatible with MS Office these last years. I'm not sure if it's 100% compatible at this point, which could be a concern for someone having to collaborate with MS Office users on the job or in business, but as a personal suite, I'd have no problem switching over to it.
Another reason I'd be against subscription services is that they are too cloud based. I like having physical control of my stuff.