Good topic. I had the same thing happen as well. Way back when (years before I joined this forum) I started with one name and couldn't make it work - the original domain wasn't available so I chose a poor substitute, and the name itself was too long and awkward. And being a very design-oriented person, it was disheartening for me when I wasn't able to turn that long name into a workable logo. So eventually it had to go.
The next name was one of those
Flash of inspiration! Oh my god is the domain available?? Yes it is woohoo! moments. I'll probably keep it forever even though I'm not doing that product now.
The one I have now is actually one that was chosen based not only on the appeal of the name but also the qualities it had. It's one of those names that sounds a little weird at first but grows on you. Like how "Google" or "Yahoo" used to sound weird but are now part of everyday speech. It was not my first choice, but it beat out many other strong contenders.
Sometimes I feel bad that I wasted time (and money) with less-than-perfect names, but I really think a name is so important for a brand, in the end I think it will be worth the trouble.
Now that I've been through that, I have actually developed a little test for each name so that I can evaluate them more easily. Here's my test if someone else wants to use it. A lot of names will die on test #1 so it saves you a lot of time.
1. Is the .com domain available? Seriously, if it's not, just forget about it.
2. Is anyone else using it for that product or similar? Just Google to find out.
3. Is it trademarked for that product or similar, in the US or Canada? If so, move on.
4. Does it accurately reflect the feel/theme/attitude/idea of the brand? If not, move on.
5. The shorter the name is, the better.
6. The easier it is to spell and pronounce, the better.
7. The more unique it is, the better.
5, 6 and 7 are more flexible but still good to keep in mind.
After you put all your names through that trial, then make a list of the survivors and get some feedback from an honest friend. Make sure to specifically ask for criticism and don't tell them your opinion of it until you hear theirs.
After you've done all that,
then you can think about each name from a more critical perspective instead of getting emotionally attached and wanting to "make it work".
Hopefully this will help others to find their perfect name faster and with less heartache.
