Where to start?

I think you are looking at this the wrong way.

You must start with YOU. It isn't about technology or systems. It's about what YOU have to offer and what you get excited about.

What are your skills? What are you at least interested in doing MORE than full-time, and not get tired of it?

This isn't about having $2,000 to start up, that will do you no good. Keep the money. Don't spend a dime until you KNOW what direction you are moving.

At this stage, since you have no idea which direction to go, you should start hanging out with people who can tell you what they need. Start going to business groups, luncheons, networking, see what types of problems interest you. Then start solving them for money.

Sure, you can start with 9x12 - lots of people are doing well with it. But it sounds like you are at absolute square zero. Before you pick a direction, I think you should get to know yourself a little better first.

Keep your eyes open for other lone-wolf operators who are just trying to make things happen. Get to know them. Have coffee with them. Shoot the shit with them, a lot. See who they really are, what kind of background they have, and if they are trustworthy.

Start doing small JV projects with the people you like. Work on stuff together, split the money, and see how it works out. After 6 months to a year, find someone to be partners with and move forward into a real business. Don't rush this. Get it right.

A few points:
1 - You will NOT make this happen at your kitchen table. You MUST get out and get to know people. You must learn to be friendly and present yourself well. Talk fast, have a good time, buy some beers, and be yourself.

2 - This is NOT going to happen as quickly as you want it to. Be prepared to spend the next year, or even TWO, before you are making really steady money. You are starting from scratch. You will not be rich by this time next year. If you are an A player, it could happen faster. But chances are you are not an A player, or you wouldn't ask for this type of guidance. I'm not insulting you. Becoming an A player takes time, discipline, and practice. You are not born an A player, you grow into one.

3 - Having a good co-founder can help you tremendously. Make sure it is a person who can work hard, for lots of hours, and get things done.

4 - Stay away from losers. They are vampires. Your business network is important. You should always be seeking to improve your status in any group. Figure out who the most prominent people are in any group, and align yourself with them. Anyone who is perpetually at the bottom, cut them out of your life. Push your way to the top with sweat and determination. People complain about the "corporate ladder" but you have to know, the ladder exists everywhere. You can ignore it - or you can just embrace it, and start climbing.

Dan's advice is awesome--he's doing better than 99.9% of the people here. Including me.

Stay away from the vampires...and get out there in front of people.

Stay behind your screen and you'll stay poor.

Most people give up far too quickly.

What is a good place to go to find local meetup groups?

Great advice from Dan.

I echo what he says - do what you are interested in doing. Whilst whatever you do needs to make money obviously, sticking at something that you're not interested in is probably doomed before you start.

I think there's three areas to make money using the Internet today; search, social and ecommerce. With your funds, unless you're a Technologist, the latter (e-commerce) is probably going to be your best bet. You don't need to go out and buy a ton of inventory tomorrow either; with Shopify and other hosted ecommerce platforms plus things like Adwords, you can experiment.

Good luck.