A rule of thumb that I follow is when I purchase a domain name I have to believe that I can flip it for a 100% profit.  So if I spend $500 on a domain I need to feel like I can sell it for no less than $1,000.  This way, even if I’m wrong in my estimation I still have some room to still turn a profit.  And if worse case comes to worse case I’ve sold domains before for a $0 profit (it happens even to the best of us).
Here's an old post on search engine roundtable that claims google's policy is to discount previous backlink juice when a domain changes ownership.  I'm not convinced whether this is actually true or something Google says to discourage excessive domain buying / 301 redirecting for SEO benefit.  The comments above seem to give varying opinions on this matter. Would be great to get to the bottom of that one!
There are many different ways to make money in the Domain Name game, but rather than skim over half a dozen of them at no great depth, Buffet takes a detailed look at Domain Flipping, one of the simplist and most effective ways to make money online. He lays out a step by step plan to guide you through the process, as well as a list of free resources that are invaluable.

Current Craze: When PokémonGo was HUGE last year, my domain flipping friends (Matt of Handshakin.com is one) were all about buying domains like PokeStopNearMe(.com) and other related domains associated with the PokémonGo craziness. It’s like the day trading of the domain world. You’re buying domains during the hype and hope to sell them for a higher price quickly before the hype fades.

As mentioned earlier, knowing the potential value of a domain name is an invaluable skill. By adhering to basic guidelines such as those I listed above and through some of your own research, you’ll be able to pick names that offer you a higher chance of flipping them more easily. Remember, a net profit of $100 is still a profit, you must start somewhere.
Flipping domains are similar to flipping houses in real estate: You buy a property with potential, improve it, and then sell quickly for twice the profit (or more). Between 2005 and 2012, internet marketers had been obsessed with flipping domains… and for good reason. Many were successful at buying plain old domain names, spicing them up with keyword-stuffed content, giving them much-needed traffic, and then selling them off to the highest bidder. But in 2017, can this still be a viable online business?
Using the keyword search feature you’d also be able to familiarize yourself with how much domains typically cost on average in a certain industry or niche. Even better, they have an addictive little app called “The Domain Game” available for iOS and Android. They basically give you a domain and you try to guess whether it sold for three, four, five or six figures. You get points for each correct answer and lose points for incorrect ones. You do this for a while and you start to see patterns. Your brain starts connecting the dots and you get better it. Now you’re ready to go out there and scout some domains!
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