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.
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.
Be careful! When searching for domains, it might be tempting to, for instance, buy mcdonalds.net (if it were available) and then try to sell it to McDonald's. The logic here would be that they own the .com and wouldn’t want anyone to own the .net and use their name, right? Also, it’s a big name so there’s gotta be a biiiiiiig payday comin’, RIGHT? Wrong, and wrong.
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:

There are several types of domain names to avoid. One is intentional misspellings, as these make it less likely someone will search for them. You also want to avoid names with extra symbols like hyphens, or with added prefixes and suffixes like "e" or "my." Outside of a few notable exceptions with very strong brands (like eBay), those additions can only hurt the value.[3]

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.

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.
Domains are more than a web address. They often have value that extends well beyond their initial registration price. Depending on how memorable it is or how well it ranks on Google, a domain that initially cost a few bucks can be worth a lot of money to the right buyer. That’s why domain auctions exist – to give domain owners an opportunity to sell their name for a profit, and give buyers a chance to get a name that can take their website to the next level.

Timothy Shim is a writer, editor, and tech geek. Starting his career in the field of Information Technology, he rapidly found his way into print and has since worked with International, regional and domestic media titles including ComputerWorld, PC.com, Business Today, and The Asian Banker. His expertise lies in the field of technology from both consumer as well as enterprise points of view.
When you see one that looks pretty good you can just click on the bid button and you’ll be taken to Go Daddy Auctions which shows some more information about the domain bidding process, how many people have bid, the traffic potential per month, the price which is now $12. How much time is left? You can make a bid. It’s based on the link profile and it’s relevancy, authority and your budget. This domain looks like a good bet for you.
Timothy Shim is a writer, editor, and tech geek. Starting his career in the field of Information Technology, he rapidly found his way into print and has since worked with International, regional and domestic media titles including ComputerWorld, PC.com, Business Today, and The Asian Banker. His expertise lies in the field of technology from both consumer as well as enterprise points of view.
Aside from places where you buy and sell domain names, there are some companies around that support the business of domain flipping. GoDaddy is one of the bigger names out there that does. There, you can not only trade domain names but also park those you’ve bought. The buying, parking and selling is relatively painless and all you must give up is a small percentage of your selling price.
Hi guys, just a thought, you do not need to build traffic to the domain yourself, you can always buy expired domains, best to subscribe to a paid service like dropping.com (so you are the first to know) or a free one, expireddomains.net and in this way, you can get old domains that have traffic. You could use these domains for parking, getting advertising income or even to sell. I have noticed, that domains that were not hot in the past, can still be hot now, just use Google Trends to type in the keyword, and you will see its future projections. 

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:

Just because something is legal does not make it ethical. While things that are legal can and often are ethical, there are practices like domain name flipping that are not ethical. Buying a domain name without intending to use it to make profit creates an unnecessary industry which costs people money and reduces general productivity and economic growth. This is the same with all practices that cost people money but do not contribute any value, most notably corruption. If we eliminated such practices our economic growth increases and general wealth is increased because our money is paying people for things that add to our lives and our communities. This does not. Evessariky reglect badly in people who choose to engage in such practices, but is a result of regulatory failure.
Domains are nonmaterial goods. When sold, the only transaction taking place is transfer of domain rights from one user to another. Barring any form of copyright or trademark violation, virtually any domain name can be bought or sold. Generic domain names, such as car.com or computer.com, are not legally protected and can therefore theoretically be reserved by anyone.
Domain names are hot commodities in today's tech-centric world. The $16 million sale of 'insure.com' to Quinstreet in 2009 may have set the world record, but even lengthier domain names are routinely sold for hundreds of dollars every day. The result is a unique opportunity for investors to invest in domain names that can be sold for a profit in the future.
This ebook is the ONLY book you need to read if you want to get into the domain name flipping game. This ebook is a step by step guide on how to get into this very lucrative online business. From picking domain names, to finding out their value, to registering them, putting them on auction sites and eventually selling them, this book takes you by the hand and walks you through the process step by step. This book gives you the websites to go to and everything! Very informative guide!
Let’s just say for example we wanted this site, crystalgiftsworld.com. It looked good based on our analysis and we’d head over to Snap Names, Nameja is another one and what these service do is they have special technology on their site that allows them to try  to register a domain on your behalf over and over again. Okay? If you tried to do that your IP would get banned, but they have some system where they know how to do it just enough to get the domain, but not enough to get blacklisted.
Content setup: If your domain has potential to attract good search engine traffic, you might want to set up some content to help facilitate that. If this helps your domain do better in the search engine rankings then it’s a big win regardless of whether you choose to flip the domain only or flip the domain with the content as a “website”. The SEO value will be helpful either way.
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.