If you buy a domain from a 3rd party, the backlinks are valuable. I always wait a few months before redirecting, so just set up a quick minisite until two page rank updates have passed and then go ahead and 301 redirect. However, it seems that you'll get the link juice from the back links, the anchor text is ignored by Google. Buying a domain at Godaddy TDName expired auctions, seem to not count as a dropped domain if you immediately set up a mini-site.
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”.
There’s an important distinction to make here between domain flipping and website flipping. The latter mainly refers to buying and selling full websites. By full websites, I mean websites that actually have content and more often than not have traffic and revenue. When buying and selling websites, the domain name matters less as the main value there is the content, traffic, revenue, history/reputation, sustainability and growth opportunities. The same can’t be said for domain names where you’re just selling “the name” and hence it’s all that really matters.