I have been in this domainig thing for over 5 years now...the most important thing I've learned is this: If you're into domaining for fun and as a hobby then thats wonderful....you surf the forums, meet others online, learns stuff about domains, brainstorm, reg some names, may be buy a few from other domainers, always talk about developing them but almost never do....

...and perhaps even sell a couple making some money. Sounds pretty good.
Now, on the other hand, if you wana take domaining as a serious business then like any other business, you need some decent capital outlay, a reasonably sound strategy, a pretty clear execution plan, and a realistic timeline....The odds of hand regging few dozen names with a total capital outlay in 3 figures and hoping to make a fat profit in less than six months are pretty much the same as playing scratch at your local convenience store.
Now addressing the original question, at least partially: If your target sale price for the domain is only in 2 or low-3 figures then most likely the name you have is such that any prospective buyer would not feel compelled to buy it having quite a few choices including hand-regging a name of about the same quality. In my candid opinion, there're probably only a couple of ways to make some serious money in this business: One, try getting on the ground floor by acquiring decent/top keyword names upon the launch of a new tld (.eu is coming soon; .xxx will be released in not too distant future), and secondly, try getting some bargains in the aftermarket and sit tight till you can sell it for at least 10 times of your purchase price....believe me its very doable, folks are still doing it even in .com (although to play with that you need a real big pot of dough)....for instance, just yesterday, I bought a .US name on Sedo for low 3 figures and I'm highly confident that one day I'd sell it for low-mid four figures. Brainstorming and hand-regging names several years after a tld's launch definitely is fun but a long shot for making money.