I probably wouldn't.
The intellectual skillset required to succeed in domaining now could be applied to several, drastically more lucrative pursuits.
Early on, you could've been a relatively shrewd amoeba and succeeded at domaining, as evidenced by a lot of the domain millionaires minted early on who rose from the ranks of garbagemen and used car salesmen. Its not that way anymore. Now, to succeed at domaining, you have to be one of those people who succeed at whatever you choose to do; if you're such a person, why fritter away your skills on this?
That's why when you examine the domaining landscape today, it looks like it does. Neither the chiefs nor the indians are much worth listening to. How many 'domain bloggers' write regularly from the vantage of authority yet haven't ever executed a five figure sale in their lives?
The short of it is this.
If you're smart enough to succeed in domaining now (and there is indeed money to be made at this) then don't waste any time here and go apply your talents elsewhere. You'll make more money. The few people who do this as Post 2003 come-lately's and actually make real money (as opposed to all the dreamers making pretend, imagination money) are either cases of wasted talent, or like me, too pathetic and lazy to take the higher path.