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.
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.
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.
Domains that are indexed on Google and highly ranked are particularly attractive to traders. Other SEO aspects, such as backlink profiles or the search volume of the keywords in domain names, also play a significant role in appraising value. Design can also positively affect the price of a domain. Short and succinct names that are easy to remember are especially advantageous. Endings are further factors that should be taken into account. Top-level domains (TLDs) such as .com or .org are by far the most sought-after endings.
That said, my recommended budget for beginners would be $500+. Using this budget you could buy a bunch of high-potential $10 domain names, expired/dropped domain names or a mix of both. It’s very important to invest only what you can afford to lose and treat this as a side hustle till you get the momentum going. As you gain experience, industry expertise and some sales under your belt, you can then consider slowly growing your business into a full-time gig.