I have an interesting twist on how I have done it in the past. I will buy a domain and use it as a development domain for blog posts and things of that nature. Then over time it will gain DA and PR. Then I will sell it off and buy another development domain and start the process over. Not quite the process you mentioned, but it works. People will link to the development site to show things off as well  sometimes, so that helps.
Yes! Selling domain is an emerging trade and no wonder if it can develop into an exchange. www.DomainX.org has been initiated with this view. There are some good ideas in the comments regarding which names to buy and how to grow their value. However one must not forget that it also involves a recurring cost (annual renewal) and keeping many of them might become difficult if you are not really selling at least a few to cover it. Enjoy free listing at DomainX.org.

The third option is the one that's the most time consuming but also has its benefits. It's like having a successful restaurant and buying another restaurant and operating them simultaneously. They're not the exact same restaurant, but both are popular in their own right and make you money. The same goes for Option #3. You could update the content on the old domain and sell the same products that you're selling on your current site. If you can get both sites to rank alongside each other in the SERPs, you're increasing your conversion chances and sales potential.
Don’t get me wrong, I’m not saying marketing your domain is not important. But, if you’ve bought a bad domain and you do (and overdo) everything laid out in this section and more, it’s still very unlikely that it would sell. It’s like spending car flipping and spending a huge amount of money, time and effort perfecting a car’s paint job, except that this car’s engine is completely fried. You’ll never be able to drive it anyway, no matter how awesome the paint job is, it’s irrelevant.
Karn Jajoo heads the premium names program for Radix’s domain extensions: .WEBSITE, .PRESS, .HOST, .SPACE, .SITE, .TECH, .ONLINE, .STORE & .FUN. Radix has made more than $1.75 million in premium domains revenue in 2017 thus far, including the biggest nTLD sale of all times — casino.online, and the sale of business.site to Google for it’s free website builder, Google My Business. Karn considers himself a new gTLD evangelist and has had articles published in The Next Web, Website Magazine, & CMO.com.

Hey, the possibilities are endless when it comes to domain flipping so do not think that all profitable domain names are already taken. At this time, almost 90 million .COM domains have been registered, so people tend to think that there are not many good domains left. That is not true since you still have the opportunity to incorporate two or three word target keywords.

Internet users, who try to find expired domains and re-register them, will soon discover that this plan cannot be manually accomplished. Professional domain traders are familiar with the registry deletion process and rely on sophisticated algorithms that indicate when a domain is about to become available. Deletion lists are the result of this research. You can find many datasets online with domains that have already become available or will soon be. You often have to pay to be able to see this information.
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.
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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