RE #2, the price issue is interesting. I could rewrite your point on #2 from a different perspective: "$20/year 'dreamhost pricing' is way too little to spend

RE #2, the price issue is interesting. I could rewrite your point on #2 from a different perspective: "$20/year 'dreamhost pricing' is way too little to spend my the blog. I'm sorry, but I rely on my blog for my entire income and so I need to know the support at the level I need is in place, the quality for the service I need is there, I have the kind of traffic that needs performance optimization and CDN, and I need to know that this is a clearly long-term viable business so you guys will be around in years to come as my blog gets even bigger. I really hope this is just the initial price plan, because I honestly believe that as you grow, it will make sense to let people host much bigger comercialized blogs on here." The point is we're simply looking at the entire blogging space and carving it up into different market segments based on needs and then super-targeting one segment. Tony Schnieder (Automattic/WordPress.com CEO) said today at TechCrunch disrupt that WordPress blogs power 8.5% of the internet's websites - so we think it's clear that one size does not fit all and there are opportunities for different services to cater for different needs. Finally don't forget there are much more expensive options out there... we're not WordPress VIP either which is several $1000's/month for service and support (TechCrunch, GigaOm etc run on this).