Re: Surface RT, Microsoft launched at the same price point as the iPad 4, but substantially later, with a last-generation CPU/GPU, non-Retina screen, and a buggy, slow, pre-release version of Office RT. That last point was inexcusable, a product management fuck up of Apple Maps proportions. The whole point of Surface RT was Office, and every review of the device said "Office RT is slow and buggy." The overwhelming feeling with Surface RT is that "I'm really going to be kicking myself in 6 months when they release the next version with flagship specs to match the flagship price."
Re: Surface Pro, Microsoft launched at a Macbook Air 11" price point, without the Air's great keyboard and with substantially weaker battery life (in Engadget's test, half the battery life of the comparably-sized Acer W700). The overwhelming feeling with Surface Pro was "I'm really going to be kicking myself when they release the next iteration with Haswell and usable battery life."
On top of all that, the segmentation was arbitrary and capricious. What's the difference between Surface RT and Surface Pro? It's an explanation that probably makes sense to a marketing guy somewhere trying to differentiate SKUs, but not one that I think resonated with consumers. Nexus 7 versus Nexus 10, iPad versus iPad Mini. That's how to do product differentiation--in a way that's immediately obvious to the consumer.
There was also some weird design choices. Why the extreme wide-format screen? Did anybody even try reading a Word document in portrait mode on the thing? I can understand the format for consumer-oriented tablets, but Surface was supposed to be a "real work" office machine! Why are there two ways to manage settings, one set in Metro and another set in the Desktop? Why do so many things require going into the Desktop anyway? Who thought it was even a good idea to expose the user to two completely different UI's in the same device?