Determine your domain's value. Before you start taking offers or listing your domain, take stock of its value so that you can come up with a good price. There are a lot factors to take into consideration when determining the value of a domain, so if you are unsure it may be wise to contact a company that performs these assessments. Some of the major factors include:
There is a misconception that good ‘.COM’ domain names are hard to find and so they are more expensive to buy. But once again, this statement holds no water. You can easily check out the ‘.COM’ domain names that are on sale at highly affordable prices. However, the only downside to flipping ‘.COM’ domain names is that you will have to discover them at different places like Flippa.com or private seller portfolios.

Yes, buying existing domain names can be profitable too. Existing domains with a potential for profit can be found using Sedo. Make sure you pick domain names that have good traffic, backlinks and Google PageRank under 17 characters. Also, steer clear of existing domain names containing special characters or numbers because they are not likely to be sold.
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.
Domain flipping is the art of buying a good domain name at a wholesale price and successfully selling it at a resale price and making a profit. I’ve been helping clients flip domain names for over 10 years. The skills needed to be successful is some working capital, knowledge of domain valuations and a good information flow from a trustworthy domain broker who knows the landscape and can help source you the best deals.
Acquiring what you believe may be a valuable domain name is the easiest part of the equation.  Finding the right  buyer is much more difficult. Using auction sites and forums is perhaps the best way to find qualified buyers that are interested in your domain, and using auctions will take some of the stress away from establishing the value of a domain name yourself.
In the grey hat SEO world, the thought is that you can take a domain that is keyword driven, do a quick optimization to get the site ranking, and sell it off at a profit. It could, and does happen daily. How much time is invested in optimizing a site to get to page one, vs how much the site will sell for? (remember that quote at the beginning of this article?). Let's put it into simple math:
  Since starting SEO back in 2009, it has become very difficult to rank brand new domains. Unless you are building a brand, it's highly recommended that you start every new money site with an expired domain. Additionally, if you're building a PBN, you should only consider using expired domains. The problem is good domains start at $50 a piece, and anyone charging less is either full of sh*t or selling garbage domains, and I mean that. If it sounds too good to be true, it probably is. DomCop has a great offer that all of you buying expired domains should consider. For the price of a couple domain names, you can use DomCop for a month, snag some excellent domain names, which would otherwise cost you thousands of dollars. If you're considering expired domain software and don't have the knowledge to program your own crawler, I'd lean towards DomCop.   
So, what I like to do is also choose DMAS listed entry. No fake or no unsure page rank. Click the apply filter button and this will show us a much better group of websites, including a lot of high page rank websites. That’s one great thing about Go Daddy Auctions that you don’t have to guess about what the rank will be which is not the case with a lot of deleted domains which, because they were deindexed they didn’t have any content, they didn’t have any hosting, they don’t have any page rank. So, you have to make an estimation.
Dictionary Word/Pronounceable/Memorable/Brandable: A dictionary word domain name is very valuable. Of course, the more popular and widely used the word is, the better. For example, “marketing.com”, “cars.com” and “hotels.com” are 7-8 figure domain names. Even if a domain name isn’t a dictionary word, being pronounceable and/or memorable and/or brandable are all big pluses that add to its value.
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