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.
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.

Use the advanced search option to quickly hone in on the type of names you are interested in. You can narrow the results by price, top-level domain (i.e, .com, .net, .org, .club, etc.), keyword, and many more filters. Using this feature will help you quickly sort through the millions of domains on the aftermarket and find the domain names that best fit your end goals.
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.
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!
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.
There are many places and ways you can purchase domain names.  You can purchase unregistered ones through sites like GoDaddy.  There are forums where people will gladly try to sell you their domain name (usually though the domains being sold in forums are either crap or the asking price is so high it does not allow you any room to flip the domain).  And then there is my favorite way of obtaining domain names, through an online auction at Namejet.  Let’s first talk about Namejet and then we’ll talk about how I personally ring the register by flipping domains.
Know your rights under the Anti-cyber squatting Consumer Protection Act (ACPA). This is the main federal law that deals with domain name trademark disputes. These distinctions are still a legal gray area, and being able to make these claims is no guarantee you will win a case. You should consult with a copyright lawyer to help determine the validity of your defense. If you are accused of cybersquatting, you may be able to keep your domain if you can make any of the following defenses in court:
The "Domain Lists" and the "TLDs" filter are now static and not created dynamic based on the current search. Turns out creating these 2 filters dynamically was slowing down the search tremendously. It even made certain requests impossible. For example now you can do a dot search that affects all .com domains and get a result with over 150mio domains in reasonable time. I'm also working on a new search cluster that will make searching even faster (not released yet).

While numbers like the ones seen above are impressive, most domains sell for significantly less extravagant prices and are generally in the two or three-digit range. Not long ago, those who were able to secure general terms (like icecream.com or pizza.com) not protected by trademark rights often found themselves sitting on virtual gold mines. The glory days of this boom have long since passed, and those looking for a profit in today’s market need a keen sense for coming trends.

HIM: "Mainly small-medium sized local businesses looking for a way to increase their ranking. Most already have a branded domain in place, and have heard that using a keyword domain can help. Or they have seen a competitor ranking using that method. The problem I face is that they don't have a lot of money to spend, so I get lowballed on the asking price. There have been a few that make a ton of profit vs what I purchased it for, but that boils down to luck: what is for sale, when I find it, things like that."


A rule of thumb that I follow is when I purchase a domain name I have to believe that I can flip it for a 100% profit.  So if I spend $500 on a domain I need to feel like I can sell it for no less than $1,000.  This way, even if I’m wrong in my estimation I still have some room to still turn a profit.  And if worse case comes to worse case I’ve sold domains before for a $0 profit (it happens even to the best of us).
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. 

You can easily find domains using the best metrics available from Ahrefs, Moz, Majestic, SEMRush, Similar Web, SEMrush, Domain Scope and Social Networks. We buy only the best, the latest, and, the most comprehensive industry wide metrics so you have the maximum amount of information to make a decision. No other tool gives you access to 90+ metrics.
Once you’ve settled on some domain name ideas, you can head over to a bulk domain search tool such as DynaDot’s to mass check all the names against different TLDs. When you’ve found one (or a few) good candidates, you can simply go ahead and register them for approximately $10 each. The next step would then be to market them. Then finally, it’s a waiting game.
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