The term flipping implies a sale that is done in a flip, or in a quick and sudden manner. You cannot be considered a domain flipper if all you do is just list your domain names and wait for years for them to sell. At its core, domain flipping is about spotting the right opportunities at the right time, involving strategic buying and selling of websites for profit.
What type of business are you considering of building something on using the domain name?Is it something you believe in and willing to put your all, how much can the monetize with the website, etc..Ask yourself much questions before proceeding to finally selling it.Also, it doesn’t matter if a different company is using a different extension.It means you have upper hand to get their traffic if you build something using the .com.Good luck
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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!
@ib2 @T-3D I've been a domain investor for over 10 years and have been very successful at it. There's a lot more that goes into it then just registering a domain name and hoping it will sell. You can list your domains on Godaddy auction listings or on premium listings, I've had a lot of success with those. Some good resources are namebio.com, dnjournal.com, namepros.com and others.

What about option #4 - Redirect your existing domain to the old domain? I bought an old domain that is 100% relevant to my current domain but currently has with very little content. It did have more content fours years ago. The old domain is 13 years old, pr=3, while my current is 7 months old pr=1 and a decent amount of content. The old domain I purchased was not expired though and I do not know if this makes a difference. What are the pros and cons of option #4? Am I correct to think that option #1 would result in no benefit from the old domain's age value and if so why is it not listed as a con, a MAJOR one. Its hard to believe that a 301 using option 1 would give my existing domain 13 years credit but I'll take it if it does.
Length: This is pretty self-explanatory. Generally the shorter the domain name, the more valuable it is. This difference in value decreases exponentially as the name gets longer, though. For instance, the difference in price between 3 and 4 letter domains are significant, while the price difference between a 7 and 8 letter domain would usually be much less significant.
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