After being around domains for over 12 years and having over 500 domains for most of that time, more domains than were ever intended to managed to slip through the cracks. At first, it was a case of selling great domains too low but more recently it has been about letting domains come too close to expiration. This can be a very bad habit if you hold a lot of domains and leave the industry for the most part for an extended period of time. Eventually, a few start to drop into redemption and then it continues unless you develop a sound renewing plan and stick to it. Nothing is more frustrating than losing a domain that you liked only because you got distracted and forgot to renew it in time.
What about auto-renewing you might ask? Well, auto-renewing brings with it its own set of problems. The first being that you may just change your mind on a domain and not want to renew it. Barring setting a standard evaluation policy, auto renewals can be more expensive and wasteful depending on the registrar. For example, if a company uses coupons like Godaddy the renewals will be at full price and may even rise as some extensions normally do. I remember buying .us domains for just $5 when they first came out, but had to renew them at $15 to 20 each years later. Yes, most of those ended up getting way.
That said, develop a schedule where you manually renew the domains you want to keep in a set period before each one expires each year. For instance, you can renew two weeks before the domain expires. That way you have a cushion before a domain slips through the cracks.
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