As the title indicates, this is a quest that we have just begun and there is still a lot of work to do before we can claim that IOTA is user friendly. In an upcoming release we will include automated re-attaching and major performance improvements for POW generation and querying the account state. Additionally, several community members have begun work on a complete redesign of the GUI wallet which we are very much looking forward to begin testing with as soon as possible.A mock-up of the new GUI Design. More information will follow soon.
As a last reminder, I would like to emphasize the point that the GUI wallet should evolve more and more into a community project which is maintained and further developed by a group of dedicated developers. We have already begun this transition, but are very much looking forward to further input from interested developers.