The exact design of the upload/insert button hasn't been finalized just yet, but making it more obviously button-like is on the list for 3.5. You can follow the discussion here: http://core.trac.wordpress.org/ticket/19956
As for "My profile" vs. "Your profile", we use second-person labels when we speak to the user throughout the admin -- the question has come up before of using "my site" or "your site" and so on, and having a consistent language throughout works better than jumping back and forth in different places in the admin.
Thanks Amy
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