Don’t forget that you’re talking 2006, so you need to be doing a lot more infrastructure work: no containers, shared hosting environments are less stable but bare metal costs a fair amount to get started, you’re using something like cfengine instead of Chef/Ansible if you aren’t setting everything up by hand, you have 10% of the RAM and no SSDs, CDNs are an expensive premium service, etc. Then think about what that means browser-wise: you can do a bit on the client side but server side rendering is a necessity and you’re still going to be burning time on browser compatibility to an extent which can be hard to remember now. HTML5 hasn’t happened yet so you’re building more stuff yourself, too.

I’m not saying there’s nothing they could have done better, just that there’s an awful lot they couldn’t have avoided at least without building a very different app.