You guys are great. You register a name with the intention of selling it asap for $200...that's what I call domain name trade. I, for one, am a total bore in that I only register names of which I think they'll be worth a lot in 10 years, and win back their reg-fee with Adsense.
Although not directly related to the topic of, "What domain do you regret not regging when it was available?", Martin40 brings up a good point.
I often have to reexamine names that I have had for a couple of years+, and my "relationship" to them before making decisions to drop/ hold, because the market and availabilities change over time. A new technology opens up, a new product hits the market, or that .com that used to be the only ext the term was registered under, begins to fill up in the other tld's. The stock on names that once received low marks, now goes up as the name ages. On the other hand, (although holding them for 10 years is a stretch),we can also be overly loyal to some of names and end up paying reg fees for several years on something that never pans out. This often is the case w/ names that are from our first group of registrations. These names, for some reason, get special priveleges and almost seem to be dwelling in their own seperate world, for, at least, the first couple of years.
"Ya gotta, know when to hold them, know when to fold them.
Know when to walk away, when the dealing's done."
Using the hold them for "10 years model", you should be pretty damn well sure that you have chosen well. Using new registrations, (and disregarding back order fees and direct purchases), let's say for instance, you purchase 10 domains a month or 120 a year. In round figures, your yearly expense is roughly $1,000. Over 10 years, your reg fees for names purchased on year 1 would be $10,000, year two- $9,000 (9years), year 8- $8,000, and so on. If you hold onto all of your names for 10 years, at the rate of buying 10 names/month, your registration fees will be $57,000 every 10 years and you will have amassed 1,200 names by the end of year 10. If you can average $5,700/year in Adsense to offset those fees, you will break even on reg fees. Remember, however, that income cannot be figured based upon 1,200 names working for you every year. Year 1 you would have 100 names, year 2- 200 names, year 3- 300, year 4- 400, and so on. Additionally, who knows what regfees will be 10 years from now or to what extent the name quality of avail names will lessen from year-year.
Based upon the expense and some of the other factors and *during this period of domain name marketing evolution*, I don't know if there are really any advantages, to using a strategy of holding a name for 10 years over the strategy of turning names over and making 25x or more of the initial outlay back (and w/o the overhead), from $200 or mid$xxx sales. The long term strategy is dependent upon appreciation and monetization and requires a a relatively large outlay, w/o any significant return on investment for, well... 10 years.