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Hi Jeff,
I know you've heard a lot from me lately, but I can't resist adding a little bit more of my gastro-acidity. I'm in a bit of a "back to basics" mode right now myself.
I think your program makes sense, especially with the added input of forum members like Steven and Linda. One thing that I notice is that you put a lot of burden on yourself. Art is a two-way street. There's you, and there's your audience. Your own estimate of your progress will change even as you reach the goals you set for yourself: it's always there, but it's never completely trustworthy. It's necessary to close the loop by exposing your work to the audience and seeing how it plays.
The audience is made up of two somewhat artificially divided parts. There's the technical audience, like the forum members, other artists, teachers, critics, etc. You're starting to make use of this resource by doing these posts. Then there's the broader audience, that responds to your work in undefined ways. I think Linda (Linda from the office, not Linda Brandon!) falls into the latter category. I want to make a point about that broader audience.
I'm guessing that Linda (from the office) has seen some of your drawings and now she wants one of them. She likes and appreciates your work as it is. I'm guessing this because the same thing has happened to me. I don't know what arrangement you've made with her, but I would suggest that, as soon as possible, you get in the habit of putting a monetary value on your work, even if it's only $5 a drawing to start. Others will see the drawing of Linda and they will want one of themselves. That's how it works. Deliver your drawings in an inexpensive but adequate mat and frame, ready to hang. Cover your costs. Everybody understands and respects this arrangement. In fact, they feel more comfortable with it: value for value.
None of this has to interfere with your personal progress toward internal artistic goals. It's just a matter of accepting that the audience has a certain sovereignty in judgement that may not coincide with your own. If things go well you'll look around one day and realize that you're a pro.
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