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.
If you buy a dropped domain from Snap or Namejet, the backlinks seem to be worthless for SEO.  They are valuable for traffic if it's targeted to your site.  Go ahead and 301 redirect into your site because it's the traffic from the back links that is worth something.  I use the Google URL builder to redirect these names so you can see the domain the traffic is coming from.

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.
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. 
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.
If you buy a dropped domain from Snap or Namejet, the backlinks seem to be worthless for SEO.  They are valuable for traffic if it's targeted to your site.  Go ahead and 301 redirect into your site because it's the traffic from the back links that is worth something.  I use the Google URL builder to redirect these names so you can see the domain the traffic is coming from.
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.
There are currently two main types of domain speculators: those that buy domains, build sites around them, and then flip the domain and accompanying website, and then there are those that buy and sell domain names without web sites attached. While both can be very lucrative businesses, the second type is much easier for novices to learn, and as such, shall be the topic of discussion for this article. 
This wonderful piece of information about buying expired domains is simply mind-blowing and I did not know about that before. It is easy for every one to understand about the topic with the pictorial representation. I feel sad that you lost around $400 due to Fake PR, but this article will surely help others save them from any sort of inconvenience.
Some buyers are a tough nut to crack and they may quote a ridiculously low offer. Explain to these buyers and convince them why the domain is worth more than the quote. If the potential buyer doesn’t agree, fret not, just move on to the next one until you find a willing buyer. Once you finalize the deal, then it’s time to find the best payment mode for the transaction.
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."
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.
The dropdate for the following TLDs is not verified. Domains might drop earlier or later: .eu .cat .aero .travel .tel .jobs .ae .at .be .bg .cr .es .fm .gd .gg .gi .gl .gs .gy .hn .ht .hu .id .im .ir .is .je .ke .kg .ky .kz .la .lu .lv .ma .mu .ng .no .om .pe .pf .pm .qa .re .ro .ru .rw .sb .sm .sn .so .st .su .sx .tc .tf .th .tl .to .ug .uy .uz .wf .yt .berlin
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.
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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