I think you're being too hard on yourself Jeff. I also think that you have a quite negative outlook on a lot of things. These two factors are always going to hold you back.

Firstly, consulting is not out of your league. You have proved this many times with the articles you have written here. Believe me, there are a lot of people who know less about WordPress than you who are charging a few hundred dollars for consultation.

Don't let a lack of skills in a certain area hold you back either. For example, you could sell themes. You could pay someone else to design them and then release them yourself and provide the support. It's not like guys like Shoemoney or Darren Rowse etc are doing everything themselves. They spend most of their time managing others.

I started making websites in 2000 but didn't make enough to go it alone until 2004. But I didn't just sit back and hope for the best. I started going to nightschool after work in 2002/2003. I also saved enough from working that I was able to take a year out in 2001/2002 and go back to University for a year to do a post grad. Perhaps college isn't for you. But what I would say is that it opens doors. It would certainly give you more options for your main job.

I think you would be able to get a much better paying job than a grocery store. I don't know your work experience or educational background but no one could possibly build a site such as this unless they were competent with computers and a competent writers.

I admit. It can be very hard to juggle work, online work, the wife and your social life. So it comes down to how much you want it. And that's something no one can teach. Unless you get the drive to go forward and the positive attitude to make it happen you'll never change your current situation.

Again, I think you just need a more positive outlook on things and believe yourself a bit more. And if you are unsure about where to go next, why not buy some books on making money online etc to give you some ideas.

On a side note, I'd love to chat with you about working on a new project. I'm sure we could come up with a good side project between us. :)

Good luck,
Kevin

p.s. I think I speak for everyone when I say that I admire your complete honesty in your post. You have been up front about a lot of personal details and asked for help and that's never easy to do.