First off, I'm not looking for this answer: "learn PHP/MySQL, JQuery, HTML/CSS...."

My background, I wear many hats, and do many things. Currently I manage investment accounts with a business partner who is also a friend. He happens to be attending business / law school perusing a joint JD and MBA. As a result, we're putting our into "coast", maintaining our current clients, but not acquiring more.

Recently I've picked up some freelance graphic design / web development / online marketing side work (Photoshop, HTML/CSS, WordPress) through some personal networks. The work is enjoyable; now I'm thinking about expanding it into a larger business with these primary goals:

1. augment my finances (I'm shooting for about $1,000-2,000 per mo.),
2. learn new technologies,
3. involve myself with meaningful work.

As an entrepreneur I don't mind the aspects of running a business that hassle other freelancers...
-- the marketing
-- the billing
-- etc.

I'm considering targeting the small to middle market businesses and organizations where I can contribute in marketing, design, and development building projects from the ground up. Thus I'll have freedom to decide the specific technology (I won't have to work with an existing code base).

What kinds of projects should I focus on? What technologies are a good fit for this style of work?

For example: It might be fun to develop with Ruby on Rails. However, maybe a lot of projects would be rolling out e-commerce solutions. Thus, I should focus on PHP due to more shopping cart options, skipping ROR entirely.