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!
The third option is the one that's the most time consuming but also has its benefits. It's like having a successful restaurant and buying another restaurant and operating them simultaneously. They're not the exact same restaurant, but both are popular in their own right and make you money. The same goes for Option #3. You could update the content on the old domain and sell the same products that you're selling on your current site. If you can get both sites to rank alongside each other in the SERPs, you're increasing your conversion chances and sales potential.
Control your expectations and keep them based on facts, data and expert opinions. Use a tool like EstiBot to get a general idea of how much the domain may be worth. Do understand that this is an automated appraisal tool, so take those numbers with a grain of salt. However, it’s great to get you started. You can also use paid, human-based appraisal services from Sedo and other providers, but these can get costly. If you’re not careful, you could easily overspend on such services and then realize your domain may not even be worth the appraisal fee.
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.
Another point of concern is that many people feel that squatting or registering domains is unethical. This is because many web developers have a hard time finding relevant domain names for their projects since most of them have already been registered. Many corporate giants also frown upon the domain flipping industry because many domain names relevant to them are already registered.
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."
That being said, many things have changed over the years. The days of MFA and quick flips are mostly gone. My advice to those new to domaining and wanting to give it a try is to take it slow, do your research, and if you do purchase a domain with the hope of turning a healthy profit - put some real time into it and build something useful. That way it's easier to monetize and easier to sell.
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.
I have an interesting twist on how I have done it in the past. I will buy a domain and use it as a development domain for blog posts and things of that nature. Then over time it will gain DA and PR. Then I will sell it off and buy another development domain and start the process over. Not quite the process you mentioned, but it works. People will link to the development site to show things off as well sometimes, so that helps.
Expired domains are domains that have been registered by individuals, businesses, or organizations, but aren’t renewed after the contract ends, or are deliberately terminated. That means that they available for re-registration. There are many reasons why someone would choose to abandon a domain; one reason could be that the web project failed, or that a domain portfolio went into liquidization. Domains can also end up becoming free due to the owner receiving warnings for possible trademark infringement. Re-registering can also result in legal consequences.
So how do you develop that instinct? NameBio maintains a database of over 500,000 historical domain sales (as of writing this post). They have interesting filtering features by which you can narrow down domains by price range, date sold, keywords and more. Simply sifting through the listings on NameBio long enough will quickly develop your domain appraisal “instinct”.