I wish I could help but I'm rather new to the whole skinning thing despite being a long time WinCE/PPC/WinMobile user.
A possible thought from things I've seen around, that may not get it EXACTLY how you like it but may be close is the HTC Home Customizer I've seen here or xda...can't remember which. I think it can do a few of the things you'd want.
The most likely thing is yo'ull have to go peace mail, and I just don't know what apps exactly to search for. Find something that allows you to put icons onto your today screen and you can find some iphone looking ones and place them for those hotkeys. You seem to have an idea for your calender. I think a thing called Phone Alarm can do the clock thing you want.
It may all be possible though simply with Wisbar Advance 3.
:\ Sorry I can't be more helpful.
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