Interesting. I've picked out some bits to comment on.

On 05/04/13 18:38, Jacob Orlowitz wrote:
Username was already taken but no warning was given. "Captcha is annoying. I've seen better login flows."
No warning given...? That's a bug.
Unfortunately captcha is a necessary compromise... It would be better to be able to get rid of it, but I'm not sure that can be done.

On 05/04/13 18:38, Jacob Orlowitz wrote:
Notice the 'html' tags when bolding a word. Would prefer a WYSIWY editor. "It feels like it could reassure me a little bit along the way. I'm not confused but I'm more engaged than I want to be. It's forcing me to pay attention and to read directions. I'm mildly disappointed in the interface. It's not the worst thing in the world. It's eh, meh. It's not like I'm going to break up with you, but... I'm not sure how long this is going to last."
Could you contact this guy again and show him how to enable VisualEditor (Preferences -> Editing -> Beta features -> Enable VisualEditor), and see how he gets along with that?

On 05/04/13 18:38, Jacob Orlowitz wrote:
Leaving a message on a user talk page: "Again I'm becoming confused. I expect a "message button or a send button or a compose button." Tried the [edit] link leading to the full page markup: "I don't feel welcome here. This feels insane." Went back to talk page. "I would like to redesign this thing. 'New section' is not working for me. Put a 'send' button near the username, or at the bottom. I'm comparing this to an email model but I want this to operate like a blog comments section."
Perhaps 'New discussion'?

On 05/04/13 18:38, Jacob Orlowitz wrote:
Signing a post: "In a million years would never have found the [~~~~] instructions. Tried to sign using markup format with ~~~~ on both sides of the text. Previewed to see that it led to a double signature and removed one. "Having to sign your own posts is ne more thing that you'd say, 'Why hasn't [Wikipedia] figured that out yet."
Until recently my Echo welcome notification message actually said "Please remember to sign any comments on talk pages with 4 tildes (~~~~)." (Admittedly this was because I didn't have any other ideas...)
However, it was changed in https://gerrit.wikimedia.org/r/#/c/56057/

Thanks,
Alex Monk