Step 1: Install Wordpress. Good, already done.
Step 2: Create a big ol' list of keywords which you think are relevant to your business. For example, [sign contract online], [sign document online], [sign contract with iPhone], [sign contract with Blackberry], etc etc. This doesn't cost anything more than your time.
Step 3: Design a template which, given a particular keyword, includes a few hundred words of content about the keyword and also acts as a landing page for your service. I'm assuming this is effectively free for most of us on HN. The last time I did it it required copy/pasting one file in Wordpress and then five minutes of hacking the PHP to do what I wanted it to do.
Step 4: Write between 50 and 100 of these, depending on how you get them done. This is what costs the $1,000, since you're probably going to zone out after doing this five times, write up the process, and then hire the rest out to freelancers.
Predicted results: on average, depending on query volumes, you're going to pick up a handful of hits for each page every month for life. So instead of having 1,400 clicks once, you'll get somewhere on the order of 400 clicks a month for forever. And instead of them being someone who was just gawking at a pretty girl in Chemistry class or poking their sheep while farming virtual cabbage, it will be someone who is right now trying to solve a problem which is costing their business money.
And if you have $2,000 to spend? It scales right on up.
And if you're savvy about how you do this? Suffice it to say that the MVP of this project gets you a wee little asset to build a business on, and implementing this strategy in a really effective way can basically carry a business on it's back. This is not limited to bingo card publishing empires, trust me.
The last thing I'd want to do is create a bunch of content that would make me look bad in the process. If I'm putting it online behind my company's name, it should be (hopefully) better writing than I could have done myself.
I mean, you could walk straight into the English Department at any university and offer them jobs for students. I guarantee you will get takers. Potential problem: the takers will be English students.
FWIW - In comparing these three methods (Content, AdWords, Facebook) based on their impact on the bottom line ($$$ -> that's what counts, right?) Facebook by far was the worst performer.
The only drawback to this is that it takes patience - results are not immediate.
I think you hit a very important aspect of this: each marketing channel (paid search, Facebook, Mobile, SEO, banners, etc.) is a tool in a toolbox. Go for what works and earns you revenue.
Paid ads yield dividends very quickly and are easily quantifiable. You can figure out what is working, weed out the bad stuff and then capitalize on opportunities. That said, SEO is also really important. While I am less inclined to go with the sparticle approach that many do, I would certainly say that writing up good information about your product in a way that relates to customers is extremely important.
The other part about your SEO content is that it is relevant to your paid ad campaigns. If you have a product that would work well for software developers and will save them money, then by all means write a good article about how awesome it is for them. Make the page a good starting lander for paid ads as well then get it to rank on SEO and drive other paid traffic to it.
In the end, each tool in your toolbox is there to make you money. Find what generates the highest ROI in the period of time you need to make it in. Focus on that and then circle back to each one down the list in turn.
Don't ever leave money on the table - your competitors won't make that mistake.
So I would have spent the $1000 on formulating a good story and reaching bloggers and journalists (which is what they did, or aimed at, in a way)
(btw what you are advocating here is an excellent idea, I just think it might not work in this case especially as they were looking to run a campaign in parallel with a conference and piggy-back on the conference name)
Edit: I did a quick check on traffic estimator, and not only is keyword search volume low, but it is very competitive. $5 per click in adwords, and the competition looks tough in the main search results:
Edit 2: a good idea would have been to buy keyword searches against 'techcrunch' and 'techcrunch disrupt'
This is also less work because you can create these optimized topical landing pages programmatically and just add some unique keyword rich content to them.
Also if you are adding domains regularly just for content you will have to wait a decent amount of time to let the domain age and you are always starting over at PR0.