Thanks for this post. I do good with Adsense and wanted to branch out so I bought 5 domains from Namejet after reading this thread. After the 5 auctions ended I spent $500 total. I contacted 30 people about these domains and after a few bites I was able to sell one of them for $500 so I got my money back and now what I sell the other four for is all profit. The best part about this is that it is not very time consuming. I spent maybe an hour on Namejet. I spent maybe two hours sending out emails. Thanks again!
Control your expectations and keep them based on facts, data and expert opinions. Use a tool like EstiBot to get a general idea of how much the domain may be worth. Do understand that this is an automated appraisal tool, so take those numbers with a grain of salt. However, it’s great to get you started. You can also use paid, human-based appraisal services from Sedo and other providers, but these can get costly. If you’re not careful, you could easily overspend on such services and then realize your domain may not even be worth the appraisal fee.
If you want to participate in a domain name auction, there are several options for how you can list your domain. Once you’ve purchased a membership, you can choose a free and simple listing, or add advanced features to increase your domain’s visibility. See our handy insider’s guide on how to list domains for sale for more details about listing a domain.
There are many risks that would-be domain investors should carefully consider before buying and selling. The three largest risks are liquidity, subjectivity and legality, but there are also many other ranging from misleading appraisals to faulty escrow payments. Would-be buyers should carefully consider these risks before investing in domain names.
Similarly, for adult items which are theme based you go for similar domain names that are suitable for such businesses. Like for bridal cakes for bachelorette we need to wish them luck sop for a bachelorette cakes and other party items site the names can be like http://www.luckonluck.com. Though somewhat it could be suitable also for book making sites. But better luck is needed to a bride after all and for HEN parties ladies need luck.
However, I'd argue that most people in the business really struggle as they don't understand what makes a good domain name and what's a bad domain name. While I do not work in this field full-time, I can say that I can make a living of it, but it's probably because I don't ask for absurd prices (e.g. randomword247.com domain name for $8000 is just unrealistic and won't happen) and therefore can sell domains easier. 
A suspiciously high number of backlinks from some related niche websites that aren’t too great in quality. In my opinion, this could be an indicator that the domain name was using a Private Blog Network (PBN) service or their own PBN to boost their authority…this blackhat tactic can work, but it places your domain name at risk and the PBN owner could pull backlinks at any time.
Domains that are indexed on Google and highly ranked are particularly attractive to traders. Other SEO aspects, such as backlink profiles or the search volume of the keywords in domain names, also play a significant role in appraising value. Design can also positively affect the price of a domain. Short and succinct names that are easy to remember are especially advantageous. Endings are further factors that should be taken into account. Top-level domains (TLDs) such as .com or .org are by far the most sought-after endings.
Surely if you purchase a domain (domain1.com) and redirect it to your existing domain (domain2.com) you expect to loose all ranking for domain1.com. If 301's are used then the objective is simply to pass on authority, not dominate the search results with 2 domains. If you want to keep domain2.com in the index then you would take Rebecca's option 2 or 3.
Please keep in mind that domain flipping isn’t child’s play. As much as you may want, it isn’t easy to buy and sell domain names for huge profits without putting in a good amount of time and effort. Although there’s nothing wrong in aspiring for at least one big deal per month, be aware that sometimes it takes months and months to sell just a single domain name.
Your course of action really depends on how much work and effort you can put into the expired domain. If you're barely able to maintain and optimize your current site, you probably want to just 301 redirect the old site (note: see my amended comment above about the link value not likely to be passed). If, however, you're more creative and have some time on your hands, you can try your hand at crafting a microsite. If you really know your stuff and are experienced at making money off various websites, you'd probably do well with the third option.
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).
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”.
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