Justin Cunningham writes what I think a lot of people experience:
It takes less time than to buy it, I don't have to deal with the broken Live login system, and the BitTorrent downloads are faster. I only know this because I had to download an ISO after one of my discs became unreadable, and Microsoft refused to replace it. Why can't I just enter my product key and download an updated ISO with slipstreamed service packs? Why do pirates have a better experience than customers? If I want to reinstall my system, or upgrade my hardware, or switch between bootcamp and virtual machines, I will.
That's how I feel. But what's critical is this:
Why do pirates have a better experience than customers?
The user experience exists at many touch points for any given product. The Windows user experience improved with Windows 7, yet here exists a failure to delight the user just to install.
Don't think about just your software. There are a multitude of interactions with your user before and even after. Expand your vision to encompass everything and you'll have a brand that is loved because it understands its users.
Just because something has always been so doesn't mean it's the best experience. It's an artefact of time and adjustment by users. Stating that things are the way they are because it's what has always been is a cop out to me.
There's always a better way. From the start & all the way to the end.
