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The biggest thing that it communicates to me is that Mike and Sam are good clients :)
Couple of quick points:
I judge the time to jump into HTML by the nature of a project:
1) Some sites deal with brand considerations – or require an approach – that is quite minimal and typographical, which lends itself well to designing within the HTML environment, although …
2) Often, I work on projects which need quite a lot of graphical design work, where I can be more productive, and feel it is more cost effective, to work in a mixture of Photoshop and Illustrator, and then layout a design in Fireworks.
There will always be a point when it is right to jump into HTML – could be straight away, could be when some intensive graphical considerations have been resolved and signed-off.
I agree on how you approach experience variations per browser. I, like most, take into consideration the time it will take for me to ‘patch thinks up’ in older browsers when coming up with costs for a project, so – If the client is happy with my quote – I will do all I can to try and get things working and displaying “as close as possible” in the likes of IE6/7 and the like.
My sites, at this stage, are not heavily reliant enough on advanced CSS3 (through choice) to mean massive problems in finding appropriate alternative methods and solutions in older browsers. But, at the same time, I refuse to allow older browsers to stop me adopting new methods – which it seems many people are. Onwards and upwards!