Someone above said to read, read, read which I totally agree with.
I'm a relative newcomer to this business as well, I admit I do not know that much about it yet, compared to many of the very experienced hands here, yet everyone has to start from somewhere.
Depending on your background, you can too, pull in other resources from your life and history.
Just because one is fairly new to domaining, does not mean that you have no intuitive knowledge upon this subject. Myself, I was in business for a great many years in the cut and thrust world of life in the United Kingdom, where at the best of times, you generally live life on the edge of the envelope, or get eaten up by some bigger shark. This teaches you shrewdness and gives you the ability to trust your gut instincts when coming across a name or any business propisition, which you feel may be worthy of some further action.
To evaluate such a name is difficult I agree. On the one hand, you want top dollar for it, because you see the vision of how it could be used, whilst on the other hand, connecting with your absolutely ideal potential end user, is altogether a different matter. In the meantime you may have to part with your name for a sum of money that does not meet your expectations, but at the end of the day, many trades are caught in this predicament. Sometimes, depending on the circumstances, it's better to simply do a quick flip, which at least will give you further income upon which to reinvest in other names, as you hone your specific skill and/or niche area.
As for the argument of handpicked names and new hand registrations not being worth very much, without causing offense, I think this line of reasoning is complete poppycock and balderdash.
What is mean't here is that certainly, yes, many of the most popular names have gone, fair dinkum, however, the english language is vast enough and the key domain prefixes, are plentiful enough that I can hardly see how it is possible to actually run out of very good key names, which too, could still command a good price.
The limiting of imagination to look at niche markets across a broad spectrum of subjects makes available a myriad of possibilities, without even delving into the world of crap name choice. Add this to the number of language options at your fingertips and the world can still be your oyster.
On coming to deciding a price, usually commonsense will give you a very good indicator, as I said, this is perhaps easier, if you have been in business for yourself and you can then, usually attach what you think is a fair value on an item at both wholesale and retail.
DNJournal offers a wealth of knowledge and I would encourage you, like me, to simply read as much as you can on high quality material related to this subject. Before long, you will come more to grips upon how to price names accordingly.
Even mistakes are good at the beginning, for at least they teach you in the early stages, what could perhaps be, a more costly mistake later on.
Best thing you can do if you are new to this, is to be as shrewd as possible, keep a level head on your shoulders, approach all of this with a good degree of commonsense, to avoid needless and wasteful risk taking exercises that do not pay the dividends you are searching for. Do not worry, those dividends will come, with the more knowledge that you acquire.
Read, read and then read some more and you will do just fine. Just believe in yourself.
Wishing you all the best and good luck.
Mark