Surely if you purchase a domain (domain1.com) and redirect it to your existing domain (domain2.com) you expect to loose all ranking for domain1.com. If 301's are used then the objective is simply to pass on authority, not dominate the search results with 2 domains. If you want to keep domain2.com in the index then you would take Rebecca's option 2 or 3.
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!

If the third party in question does not have the trademark rights they claim, or it is not a very strong claim. In most cases, the third party will need their trademark registered with the US Patent and Trademark Office (USPTO). The USPTO website has a trademark search engine that you can consult. This may also require a cybersquatting attorney to help determine if the trademark claim is strong enough.
Yes! Selling domain is an emerging trade and no wonder if it can develop into an exchange. www.DomainX.org has been initiated with this view. There are some good ideas in the comments regarding which names to buy and how to grow their value. However one must not forget that it also involves a recurring cost (annual renewal) and keeping many of them might become difficult if you are not really selling at least a few to cover it. Enjoy free listing at DomainX.org.
Here's a test I have in process.  I bought an old $5 closeout domain from Godaddy TDname expired auction.  I put a quick minisite up and linked to it with a crazy anchor text phrase.  The domain is ranking for that crazy term now.  It's gone through one pagerank update and I'm waiting for a second to come.  Then I'll redirect the domain to another minisite.  I suspect the second site won't rank for the anhor text, but we'll see.  

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Keyword relevancy is not the only thing that matters when it comes to SEO. However, domain names that were previously used by other businesses usually have a lot of backlinks and a decent ranking on PageRank. Even though such domain names are usually about to expire, they are still worth a lot of money if they have a good number of backlinks and a ranking of five or more.
A suspiciously high number of backlinks from some related niche websites that aren’t too great in quality. In my opinion, this could be an indicator that the domain name was using a Private Blog Network (PBN) service or their own PBN to boost their authority…this blackhat tactic can work, but it places your domain name at risk and the PBN owner could pull backlinks at any time.
Here’s what you DON’T want to do: Target prospective buyers based on their perceived economic status, without any insight into the industry you’re targeting. “Lawyers seem to do well,” you think, “maybe I should start selling names to them.” So you rush out and buy a bunch of domain names you think would appeal to the law firms you’ve identified as potential buyers. Without knowledge of the space, you may not know that the American Bar Association and other industry-specific organizations set rules that govern some aspects of legal advertising. You’re not going to strike gold selling names your target buyers can’t use.

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.
Current Craze: When PokémonGo was HUGE last year, my domain flipping friends (Matt of Handshakin.com is one) were all about buying domains like PokeStopNearMe(.com) and other related domains associated with the PokémonGo craziness. It’s like the day trading of the domain world. You’re buying domains during the hype and hope to sell them for a higher price quickly before the hype fades.

You can’t tell us (with a straight face) that aged dictionary word .net and .org domains won’t sell easily. The .net extension is technically OLDER than .com, and holds an equally intrinsic value to that of its .com counterpart. These LLLL .com’s that are just letters slapped together may be cute to look at and easy to sell, but in the eyes of Google, ANY aged domain that makes sense (i.e. a dictionary word) is going to be much easier to rank for than some acronym or hodgepodge .com…and at the end of the day, that holds more value than whatever society sees in these nonsensical “wqij.com” names.
As mentioned earlier, knowing the potential value of a domain name is an invaluable skill. By adhering to basic guidelines such as those I listed above and through some of your own research, you’ll be able to pick names that offer you a higher chance of flipping them more easily. Remember, a net profit of $100 is still a profit, you must start somewhere.
What I like to do is sort by DP which stands for domain pop, and this is basically the number of linking root domains. So, BL is the number of back links. As you know that can be somewhat misleading if they have a lot of site wide links or multiple links from the same domain. I like to sort by domain pop. What that does is it brings up the sites with the most amount of referring domains.
Instead of focusing on one domain name to sell quickly, try selling large volumes of domain names over longer periods of time. While this may require a more substantial investment, it will also return a greater profit in the long term. Remember, if you follow the basic principles of domain name speculation, there is good chance that your domain names will sell eventually.
The easiest and least time consuming option is to 301 redirect the old domain to your existing site. This tactic obviously works best if both sites are in the same sector and are targeting the same keywords; otherwise, if you have a pet supply site and you buy an old Texas Hold 'Em poker site, a redirect probably might raise some eyebrows among the search engines. If, however, your site is brandnamepets.com and you buy onlinepetsupply.com and 301 redirect the domain over, you're inheriting a lot of topical and appropriate links.
If you’re serious about domain flipping, one of the best strategies is to buy expiring domains that auctioned on the market such as GoDaddy Auctions. Make sure you pick domain names that have good traffic, backlinks and SEO metrics, or domains with the generic niche. Expiring domains with a potential for profit can be found using BuycomDomain.com, this is a free website/tool that helps you sort through the domains by different metrics (age, traffic, backlinks, domain authority etc).
Listen to expert domainers on domainsherpa.com. Read anything by Michael Berkens, Frank Schilling, Eliot Silver, Morgan Linton, and Ron Jackson. Watch YouTube videos on domain investing. Read blogs like The Industry News Magazine at DNJournal.com. Search #domains on Twitter. Go to industry conferences. Understand the Google Keyword Planner tool inside and out.
These should be more than enough to get your domain in front of tons of potential buyers. If you did a good job picking an awesome domain, you should have no problem (eventually) selling it. You need to be very patient as it could take months or even more to land a decent deal. A lot of domainers sit on domains for years before actually selling them. This is why it’s best not to obsess over a domain and simply move on with buying and listing others (or going back to your day job if this is a side gig) once you've listed the initial one.
Keyword relevancy is not the only thing that matters when it comes to SEO. However, domain names that were previously used by other businesses usually have a lot of backlinks and a decent ranking on PageRank. Even though such domain names are usually about to expire, they are still worth a lot of money if they have a good number of backlinks and a ranking of five or more.

There’s an important distinction to make here between domain flipping and website flipping. The latter mainly refers to buying and selling full websites. By full websites, I mean websites that actually have content and more often than not have traffic and revenue. When buying and selling websites, the domain name matters less as the main value there is the content, traffic, revenue, history/reputation, sustainability and growth opportunities. The same can’t be said for domain names where you’re just selling “the name” and hence it’s all that really matters.

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