The second option requires a bit more time and effort than a 301 redirect. You could do a mini overhaul of the site and turn it into a microsite for your main domain. This option is good for exact-match domains for your targeted keyword, and there are other reasons for going the microsite route that Rand's highlighted in his post about root domains, subdomains, subfolders and microsites. This strategy also works better if the old domain has decent rankings for the keywords you're targeting. 

Buying and selling Domains is a tricky industry. You easily get addicted to it without really knowing what it's all about. Unfortunately I learnt a lot of the answers on here after losing 6k on useless domains. It is a constantly changing industry but the subject that keeps coming up is TRAFFIC. Organic type in Traffic. Those premium domains are long gone and you need to spend big bucks to acquire them on secondary markets such as Domain Auctions, Expired Domain Names, and Available Aftermarket Domain Names for Sale but if you keep up to date with future trends then you can spend less on hand registered names. You really need to think outside the box and spend a lot of your time reading industry leading blogs like business insider, network as much as you can and have a specific niche before jumping into other trends that you don't quite understand. There's so many ways of selling. Don't try and sell to other people who are trading domains aka domainers instead look for an enduser on Google by typing the name you own and if there's advertisers then you have yourself some leads or use tools such as Free Domain Appraisal and Domain Productivity Tools. A buyer can be convinced to buy if you have the numbers to prove how much that domain would be worth to them. Find out how much they spend on advertising per month then make comparisons with the number of direct type in traffic they get from your domain that you selling. If you can prove these numbers then it's easier to sell otherwise you better off holding on to it, maybe develop it the way Trump has developed his name until someone interested gets in touch. There's so many platforms where you can list the domain such as The world's leading domain marketplace , Park Domains - Afternic -DomainNameSales.com etc . Please NOTE  I am not promoting any of these services but I have used them before and have had some success. Probably should have signed up for their  affiliate programs but haven't had a chance before this question came up. There's so many other metrics involved  so research as much as you can, don't spend a day without reading about the subject and go in at least knowing what you are doing. My two cents.
Building a solid domain portfolio is not a piece of cake; it may take you several months or years to achieve this goal but it will definitely be worth it in the end. When you are in the fishing phase, look at the potential of the domain name. Another common strategy used by seasoned domain flippers is to get hold of some high profile domain names and sit on them until they soar in terms of value.
It’s also not so easy to manually re-register. This is due to backorder providers which are paid to keep an eye on expiring domains over a certain period of time and then register them for the customer as soon as they become available. Promising expired domains are therefore usually sold before they have a chance to be put back on the registry menu for the public to look through.
I remember the glory days of the Internet where people did make a ton of money buying domain names. Until I came across this post I actually didn't even realize that people actually still thought they could.make.a.lot of money by doing this. I have some domains that people would be interested in buying and I get contacted about them but mostly it is for people wanting to purchase them for like $1200. And for that price I would rather just hang on to the domain name. I also get contacted by a lot of people offering to sell me complimentary domain names at what I would call ridiculous premiums. The knew google is all about branding. I would consider paying for a domain name that has a great brand attached to it but I could care less about most keyword rich domain names. Of course there are always exceptions.
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.
To find popular phrases I opened up the Google Keyword Planner. This free tool by Google, allows you to find out how often a word or phrase is searched in Google. A phrase like “Yoga Mat’ has on average, about 10K – 100k monthly searches. That’s A LOT. However a more niche phrase like “Good Yoga Mats” only has 100 – 1K monthly searches. These seem similar, but I wanted to focus on the exact popular phrase that people are searching for.

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. 
If you are looking to monetize an idle domain, looking to third-party platforms would be a good idea. Many of these platforms such as Nameforest ourselves will create a logo alongside your domain, which will be added to the list of preexisting domains on their sites. This is useful as the demand for your domain will also be greatly increased after it is rented as opposed to a domain that leads to a blank site - thus making it easier for you to find a potential buyer.

I have a question regarding a certain keyword though generic but it is trademarked and the trademark owner asked me to remove the parking page, is there a way i can offer my domain name to the company? What is the best approach in selling the domain to him without hard selling it and giving a reasonable price. I will be giving 10% commision to any domainer-mate that can help me pull the sale off.

Expired domains are especially attractive due to key SEO factors that are primarily associated with an existing backlink profile. If you are considering buying an expired domain, you can determine the quality of it by looking at the inbound links. When it comes to assessing the value of an expired domain relevant keywords contained in the second-level domain, a possible reference to products, brands, or services are all useful.

I recommend Go Daddy premium and Afternic. Once you get it listed at those two places then do a redirect so that anyone who types the URL goes to one of those two, for-sale pages. I would suggest a price of $500 to $2,000. You might get lucky and attract a buyer in the next year or two. After two years, if it doesn’t sell I would just stop renewing it.
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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