Tom, here are my thoughts.
1.  Windows seven 32 bit machine.  As much ram and multi-core processor 
power as you can get.
KathyAnne's An Emirsion in to windows 7 is quite a good resource.
Once you get used to it, their are things you will like.
As far as e-mail, I haven't tried hooking up g-mail to windows live, 
outlook, or thunderbird.
Leting go of our standard menu system makes a bit of learning curve, I'd 
take the advice of jaws users on that issue.
The reason I suggest 32 bit is to reduce the possibility of driver 
incompatability.  Their is no way I have found to get a 16 bit dos prompt in 
windows 7, if that is something you need, like I still do.
My database for resources is still q&a, I haven't figured out anything that 
will work as well.  If anybody has an idea I'd like to talk to them.