The Esperanto community tends to be specially resistant to reforms - so a lot of proposals like Esperanto II and Ido have not achieved much. On the other hand, natural languages suffer occasional reforms, like the recent cases of German and Portuguese.
For instance, let's take the polemic diacritics letters: ŭ, ĥ, ĉ, ĵ, ŝ and ĝ, that, in my humble opinion, pose an unnecessary difficulty to newcomers. Most esperantists (myself included) argue that the diacritics are easy to get along with the 'h-' or 'x-' system, or even adapting the keyboard accordingly. But most search engines, including the browser search, does not distinguish between 's' and 'ŝ', so it IS a nuisance somewhat. The Esperanto learning curve is not optimized with these letters, and the interest on the language inevitably fades. It would be easy to replace the rare ĥ with 'k' or 'h', ŭ is the equivalent of 'w' in most European languages, and there are solutions for the other letters that does not belong to this question but would simplify the phonetic and orthography of Esperanto without hurting its community.
So, considering there are some room to evolution, what would be the process of proposing a spelling reform? How to maximize the chance of being seriously considered? Are there any examples of a similar and recent proposal that was considered by the community or any Esperanto organization?