Also with the domains, a name which can be cheap for one can be worth gold for the other. Permute the letters in your domain name and try contacting and eventually selling out to organizations that run under those names or contain the letters within. Companies would be keenly interested in buying out the domain names that matches the product's name. Hint : Look for companies on LinkedIn
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.
Check backlink profile: If you’re not familiar with what backlinks are, they’re basically any public website that “links” to the domain in question. Since there are numerous shady tactics in the SEO world, expired domains’ backlink profiles should be examined carefully. Check if too many links are coming from the same domain or if links have weird anchor texts/use foreign languages. You can use a tool such as ahrefs for these purposes.
If you buy a dropped domain from Snap or Namejet, the backlinks seem to be worthless for SEO.  They are valuable for traffic if it's targeted to your site.  Go ahead and 301 redirect into your site because it's the traffic from the back links that is worth something.  I use the Google URL builder to redirect these names so you can see the domain the traffic is coming from.
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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. 
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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