A teacher might not be fully what you need at this point - I suggest starting with an instructional designer (someone that knows how to teach but has additional skills in organizing information and the tools/mediums used for learning today). You're touching on a few great concepts that are being addressed in corporate learning and education settings with supporting technologies right now - nano-coaching (short interactions with a coach/mentor that already knows how to do the shit you are trying to learn - like evaluating a work product relative to the skill - for example, sampling and providing feedback on a mead you brewed, or the recipe you plan to use, as part of going through a brewing learning path), user-generated content (allow the people going through the experience come up with new resources like a link to a great article or video), curated content (have the expert on a particular topic differentiate really good content from crap, but balance that with user ratings of content to let the better stuff rise to the top and the other stuff to sink down), a way to provide a self-selected learning path (organizing the content - you are hitting on competencies/activities that build skills in those competencies), certification (by having some organization/structure behind this it might mean something to someone else), and even the most recent hot topic in my industry right now that I am not completely sure the best use of, badging (as you go through these different experiences you earn badges as an indication of your proficiency level in certain skills - rolling up different skills into some form of indication of mastery of a certain topic).
Flipping to the technology side - there is an emerging standard that underpins what I was talking about above known as TinCan API or Experience API (xAPI). It is a repository of statements such as <actor> <verb> <subject> like "Paul listened to Podcast 152". This allows the tracking and reporting under some of the concepts above like badging and tracking the results of the coaching...like did the coach pass the student on the task - or did they provide feedback and recommend they try again. I once worked with someone who has put this standard into a tool that they are selling to corporations, and from what I have seen of the tool it could give you a better idea of what I am talking about above. Real small company, doing some smart things - Cognitive Advisors and the tool is called Trek Learning Experience Manager - http://www.cognitiveadvisors.com/trek