Here's my take...I started online in 2005 and my first site outta the gate was a huge success for me. I'll fully admit that it combined a little luck, hard work, and some good teaching.
I personally think that 2004-2006 was kind of a perfect time to get online...granted, I wouldn't have minded doing it a little sooner. But it definitely seemed like a lot of good marketing products and information (PPC, SEO, testing, SiteBuilders), so it took away the learning curve associated with making money. Back then, an average webmaster didn't know much about SEO, PPC, Analytics, Site Design, etc. Now, it's not uncommon to have some kind of base level of knowledge. The sites I used to compete with (including mine) were so ugly. Now, new competitors come on board with much slicker looking sites.
Personally, overall I DO think it is harder now than it used to be. Back then, a little knowledge went a REALLY long way. Now the increase in competition is making it more likely that others are at least aware what's going on.
Still though, as hope to most of the newbies, most of my competitors are still pretty clueless. It's just harder because there are more of them taking up space (In the SERPs or PPC or whatever). They have analytics installed, but don't have a clue what to do with it. They read about SEO, but they do the basics. They use PPC, but probably don't isolate that traffic to see if it's profitable. And as hard as it is to believe, most of them still don't really use email all that much.
So what do you think?