No. of Recommendations: 0

The part that's freaking me out is this: when I started my job in 2004, I worked as an independent contractor for six months. Of course, I didn't put away the SE tax that I knew I was going to have to pay, so when tax time came, I ended up doing my taxes sort-of, realizing that I had about $6k to pay, filing an extension and paying about $1000 of the estimated balance.

You really do need to see a bean counter who knows the ins and outs of self-employed contracting, which should be just about any reasonably experienced tax preparer. There are lots and lots of deductible expenses available that you do not know about, which come off the top of your gross, and which will save you lots of tax $.... even without getting too aggressive about interpreting things, which in your case might not be as good an idea as it usually is, given that you may be up for review here -

I've been consulting off and on for years, and give this advice to everybody I know who is starting out in this game - and everybody who has followed this advice has saved thousands!

Good Luck!

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