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!
In today's SEO (2015) the answer would be a big no! With changes to the google algorithm and the constant updates panda, penguin, what's next...., much of the "keyword url" power is now gone. While there was a day when it made sense to buy a good named .com and expect instant indexing, not so anymore unless the site is very strong coming in ,which in that case you'll drop a minimum $50k. If you are willing to drop that kind of money and the site has a high domain authority, it might make sense as long as it matches whatever product or service that you're trying to sell. Just my opinion...
A good majority of web developers view the domain flipping industry with disdain as they face a hard time finding the right domain names for their own development projects. Domain flipping is also looked down upon by corporate and business entities who register multiple domains related to their trademarks or business names. Actually, it is these people who’re the real domain name squatters!
Domains are more than a web address. They often have value that extends well beyond their initial registration price. Depending on how memorable it is or how well it ranks on Google, a domain that initially cost a few bucks can be worth a lot of money to the right buyer. That’s why domain auctions exist – to give domain owners an opportunity to sell their name for a profit, and give buyers a chance to get a name that can take their website to the next level.
There's a lot of guesswork that goes into domain name investing. It's not enough to purchase domain names that are currently popular. Just like a stock, coming too late to the game won't be profitable. You have to think of the future, instead. What domain names might be profitable in the future? Is there a new product or service that may become a huge hit? Where is the future headed?
The second option requires a bit more time and effort than a 301 redirect. You could do a mini overhaul of the site and turn it into a microsite for your main domain. This option is good for exact-match domains for your targeted keyword, and there are other reasons for going the microsite route that Rand's highlighted in his post about root domains, subdomains, subfolders and microsites. This strategy also works better if the old domain has decent rankings for the keywords you're targeting.
GoDaddy’s domain auction space serves as a “marketplace” for buyers and sellers to get together and make deals. When a domain expires, it typically goes right back to the registry. If it’s a valuable domain name, however, registrars will try to sell it through auction, and buyers are always eager to capitalize on potential deals. Participating in a domain auction can be a nuanced business, so take a look at our Auctions FAQ page for more details on the process.
I did this last month, snagged a great domain that no one else found and got it for $69 because I waited until the last moment to place my pre-bid. Flipped it within a week for a little over $1,000. And probably could have gotten more if I sat back and waited 6-12 months, but a bird in the hand… (plus I like to keep turning over inventory and maintaining cash flow).
Mr. Dabir as far as my knowledge is concerned such media oriented names are of premium category and may seek higher value. I was acquainted with discussions going on regarding primarily hindi language entertainment platform called http://hindi.media and the dealing was of higher end hence expect it to be in several thousands bucks. Any inferior expectation may beget only disappointment.
Hi I totally agree with you Domaineer42. My partner and I are web developers and are seeing a lot of ‘hype’ selling and not enough ‘real value’ selling based on actual search engine criteria. Recently brokers have knocked back selling domains with great potential value based on some pie-in-the-sky logic, defying even Estibot values we’re told to use. The domains were not our best but with four figure value, according to Estibot, I thought it was a great start as a newbie to domaining. In an industry which should flourish, some of these domain ‘fashionistas’ are making rods for their own backs by devaluing domains that have REAL potential value based on customer search. I don’t understand what is going on, but I have decided to opt out for awhile. We have quite a few domains in our repository, with data backed search criteria, trending upwards. Will bring them out of the closet when the industry is ready to get real.
Link popularity: the link popularity is a parameter that is used to quantitatively evaluate incoming links to a website. This is measured depending on the number of links to a domain according to the mantra 'the more incoming links, the more important the site'. Link popularity is generally determined by the PageRank algorithm. The PageRank only plays a minor role in determining the domain’s relevance.
Your domain name registrar may provide you with a free one-page Website tool, which you can use to create a “this domain is for sale” landing page. Alternatively, you can create a single page (perhaps a hidden page hanging off one of your existing websites) that indicates that your domain names are for sale. You can then forward all of your domain names that are for sale to that one page.
I like to also click on the No Fake PR’s and No Unsure PR’s because a lot of fake page rank or page rank that’s been manipulated in the past and you want to make sure any authority that you see is real. Once you’ve picked all the criteria you want to choose, click on the apply filter button. This took our list from two million to 237. Now, even within that, that’s kind of overwhelming.

You can find the new fields in the Column Manager and the Majestic Filter Tab. Majestic Crawled URLs, Information about the Outbound Links of the Domain and Information about the types of Incoming Links (follow, homepage, ...). Also you can now see the detected language for the website (or previous website) on the domain and the language of the anchor text links referring to the domain. The filter for the website language only includes values with at least 20% and the filter for anchor texts only with at least 10%. When you hover over the column, you still see all values (even lower percentages), but lower values are not used for the filter. If you only want to see domains matching the majority language, use the "majority language" filter. Unfortunately that filter doesn't work in the domain name search
Parking the Domain Name: When you park a domain name, every time someone enters IHateCold(.com) into their web browsers, a page with a few ads and sales info is shown. So you’re letting the visitor know that the domain is for sale and you make a few cents on the ads displayed for views. There are several domain parking services for when their buying and selling domain names, but I’ll go into that in another post.
Many non-savvy internet users may not even be aware of the existence of other extensions. That said, because there are many new extensions popping up every now and then, you can often find amazing one word and 3-letter domain names with these new extensions that are otherwise almost impossible to find unregistered in the .com world. Additionally, these new extensions are becoming more and more familiar to users every day, hence it's almost certain that their value will continue to increase as time passes and wider adoption manifests. 
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