If your business is suffering from many of these then I would firstly attend to improving the IT governance ie. getting your own house in -order; as without effective IT governance you will be spending money without any real idea as to whether it will actually deliver any benefit to the business.
Secondly, IT needs to urgently talk to the business; as either the business is happy with what it has got or it just hasn't bothered to tell IT about all the stuff it's done to workaround/avoid IT. In either case to move things forward, you are likely to have some substantial issues around the contribution and role of IT (and the IT department) in the business and effecting change (in both the business and IT) to deal with, before you can get down to talking about specific technology refresh and IT-enabled business change programmes.
Aside: With respect to the desktop, without specific business needs/demands, practically the only reason to upgrade from XP/Office 2003 to Win7/Office 2010 is to ensure you continue to receive mainstream support from Microsoft on critical desktop software and to take advantage of software you've already paid for (if if you have a Volume License agreement). With business involvement, the upgrade provides the opportunity to deliver so much more (namely IT-enabled business change) ...
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