I have a terrific name portfolio and have made a second salary on names. But I spend almost no time on the search/acquisition. I just keep my eyes open!
Some stuff to keep an eye on:
* trademark. New domainers, please don't go buy a name containing someone's trademark. There simply is no excuse and you will lose the name (without compensation and possibly with legal costs). And if you think you can just "flip" a name with a trademark to someone else and run with the money, think again. You can still be liable for damages caused AFTER you sold the name. You essentially become an accessory to a crime. Not worth it!
* private name registrations overconfidence. It's a simple matter to get access to the real owner of a name with the right legal paperwork. This is not a good hiding place.
* Only Invest in dot-com. If you can buy a good non-dot-com at street price, hey, go for it. But the non-dot-com names need to be highly strategic (e.g. completing a name packages) if you're spending much on them.
* Avoid Administrative Overhead. Get all your names on a system that automates your domain renewals and use a tool to keep track of the whole list. If you end up spending hours a week just doing administrative crap, you're losing money in time.
* Be careful if you've ever dabbled in Afternic or Sedo. Make sure you keep all of your prices consistent and up-to-date. If the value of your name has gone up, and your price is years old on one of the auction site, you just reduced the perceived value of the name to the buyer.
* lock all names and whitelist your registrar's domain name. I use an outlook rule to put up a big alert when any kind of message about a name comes in.
* I think Dba's are better than private registrations and look more professional and less spooky. Get a dba for your corporation, call it "acme domain holdings inc." and put it on the names. Use firstname.lastname@example.org your email and have it filtered by spamstopshere.com There is no better spam filter on the market.
* Use Form Filler Tools. Save yourself hours by using roboform to fill in information during registration and other administrative tasks.
* Use escrow.com. If a buyer won't do pre-pay, use escrow.com and make them foot the bill. It's usually about $30-50.
* Don't sign long contracts. Domain sales should be simple. If they won't use a simple letter, tell them you need to add $200 to the sale to cover the costs of having your attorney review the agreement. I was handed a FOUR page domain sale agreement once. I grumbled. The contract became a one page letter 2 days later. Done deal, everyone's happy. It turns out that the reasons many sales agreements are so long for domains is many attorneys have never been involved in a domain sale before. I later found out the 4 pager was a boilerplate for the sale of a PATENT!
Some government organizations may want you to sign a "single source letter" which is cool. This is because they usually have to get three bids on things, but for domains there is only one source - you. These are usually really simple and you can't get around them. It's also cool to sign something saying that you are the only one who owns a name. Nobody wants to hear about a secret owner coming out of the woodwork later. My Godaddy rep did a nice job answering questions on a large $ sale for me. I just conferenced him in with the "confused" buyer and let them ask about what constituted ownership. This shows I have nothing to hide.
* Don't let big $$$ make you stupid. When money is being exchanged, some folks' writing hand goes into "sign whatever" mode. Once the buyer tried to slip in text that said they could ask for their money back anytime within 90 days as an addendum.
* Don't actually transfer the name until your bank shows their check amount went in and cleared. This happens electronically and you should be able to see it within 24 hours at most banks. Cashiers checks should make it faster but they don't usually.
* Actually have the buyer take the name to a different registrar account and remove you completely from the contacts. Make this an open and closed deal. DO NOT remain connected to the domain name you just sold or you might find yourself in a mixed up pile of crap someday. Send a confirmation of completed transfer via registered mail or just use email and ask for a reply.
Hope those tips help!