The market-driven principles of the domain trade mean that a domain is only worth as much as the buyer is willing to pay. It is for this reason that criteria such as market potential and usability play such central roles in determining prices. Values can change at the drop of a hat. The price of a domain that was once of little interest to anyone in years past can skyrocket once, for example, a newly founded company takes interest in that same name.
I remember the glory days of the Internet where people did make a ton of money buying domain names. Until I came across this post I actually didn't even realize that people actually still thought they could.make.a.lot of money by doing this. I have some domains that people would be interested in buying and I get contacted about them but mostly it is for people wanting to purchase them for like $1200. And for that price I would rather just hang on to the domain name. I also get contacted by a lot of people offering to sell me complimentary domain names at what I would call ridiculous premiums. The knew google is all about branding. I would consider paying for a domain name that has a great brand attached to it but I could care less about most keyword rich domain names. Of course there are always exceptions.
The IP popularity and domain popularity each play a part in the overall quality evaluation. If you come across an expired domain with a high link popularity (i.e. a large number of backlinks), but then poor values when it comes to IP and domain popularity, you can assume that these links were obtained in an artificial way. Domains like these will have already caught the search engines’ attention. Perhaps this is the reason why the domain was abandoned. Users that want to start a serious online project should steer clear of these domains.
If you know how to get websites to page one, why are you not marketing that fact to potential clients and consumers or would-be domain purchasers? Trying to get a keyword driven domain to rank high and sell it off for a profit isn't a good investment, either time wise or for the long-term success of your company. Instead, use sites that you have already ranked high as an example of how awesome you are and sign them up for a monthly fee, rather than trying to sell them a "make money now" domain.
So how do you develop that instinct? NameBio maintains a database of over 500,000 historical domain sales (as of writing this post). They have interesting filtering features by which you can narrow down domains by price range, date sold, keywords and more. Simply sifting through the listings on NameBio long enough will quickly develop your domain appraisal “instinct”.