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Or maybe just look at deleting names which happens every day and pick one which actually means something... pool.com, namejet.com and snapnames.com.
This sounds like a cool idea, but after looking at it, I think the odds that you'll come across something better than brute-forcing could produce seems a little low. I mean, let's look at the most realistic deleting names on the list today. I'm actually selecting the least nonsensical ones here (e.g., not the long list of names like "o6fg29ra.com"):

cafebrucenyc.com, dubai-companion.de, obamacoolbrother.com, raceto11.com, oasistaxi.com, wacko.us (this last one was actually the best I saw on the whole list)

a decent deleted name could potentially cost more at auction as buying from a squatter.
How do you check if domains are available? I searched a little for a domain name API not too long ago, but all I found were things that required you to sign up (and almost always pay money, I think).
The quickest way, without hammering anyone's server is to download the Verisign zone file daily and just search it.

They frown on using it for domain lookups, but you might be able to get access anyway.

bustaname just uses a DNS lookup for an A record at the root of the domain. they say it's not 100% reliable but it's much faster than whois and i guess they don't want to use the zone file.
You can do Whois lookups. This standard is as old as the Internet.
DNS is much faster. whois is usually rate limited and a lot of whois services have restrictions on automated querying. Obviously, whois is more accurate though.

So. When I need to test if a bunch of domain names exist, I first of all do a DNS NS lookup. If you get a result, you know the domain exists. If you don't get a result, then do a whois.

We'll have one soon at http://iwantmyname.com

The only reliable way for domain checks is to query the registry database directly through a registrar instead of going through whois / DNS.

Thanks! This tool is such an easy thing, and still extremely useful. Will use it for my own domain searches in the future.
I just registered a matching .com and.org that I got from here, and they don't even sound Web 2.0-y.