iPads CAN handle proxies, you just can't lock the proxy details in via profiles using Apple's iPhone Configuration Utility. They have to be entered manually after the profile has been installed.
Surely SIMS would sit far more happily on an Acer Windows Tablet than on a iPad (unless you're using a web-only version of SIMS, of course, when it makes stuff-all difference). Shared calendars, meeting requests, etc aren't a feature unique to the iPad - Exchange does this, as does Google Calendar and presumably your Live@edu set-up already includes it.
As with any product selection, you need to take a step back from what the user wants and look at what the user needs. The interest in iPads could come because a) they're Apple fans, b) they want to appear high-tech/modern/progressive, c) they heard about another Head using an iPad so want one, d) they heard about another Head using an iPad and think it would be useful, e) something else I've not thought of. None of those are actually reasons to get the iPads. Look at what they need to do as an end-user and how best you as IT manager can deliver that to them; consider the fact that by saying "I'm not getting you iPads which I don't understand/are hard to manage, but I'll get you a Windows Tablet instead" you could actually give them a better experience than if you blindly bought the iPad. You may conclude that the iPad is actually the way to go, but I do think it is your job to investigate other options.
There are a couple of articles in ICT Review magazine (a PC Pro mag I seem to have gotten on the list for - Education | PC Pro) comparing different tablets and looking at how to use them in education.

A head and the deputy came to me today and said they thought they needed ipads so I said I'd need one to enable me to support them and to evalulate for SEN use !
(To be fair, after about 60 seconds, I'd convinced the deputy that maybe what they needed was a new slim laptop as an IPad is like a 10 inch nettbook with the keyboard )
But I may still get one
The wife will be pleased - She'll be able to farm and watch Bargain Hunt at the same time
Si
In all seriousness, if it is your job to support and train users on all aspects of their IT equipment, then you need to be bought one if someone else is getting one. I tend to draw the line between whole-school and departmental resources, so will help with Office, SIMS, Photoshop, etc but not AQA eScience, French Big Books, etc. If I happen to know the answer, I will of course help, but I won't subsequently go looking for the answer with department-specific software.
My thoughts exactly...
I was invited into an SMT meeting about this a while back. I gave all the SMT members a pen and pad and asked them to write down why they needed iPads.
They duly wrote down what, why, and where - not leaving anything out. I then tore the top sheets off, threw them away and told them that they worked far harder, smarter and agreed on things far quicker using a pen and paper.
My Headmaster knew what I was doing and sanctioned it beforehand.
Needless to say, our SMT do not ask for 'new toys' anymore........

I Thought you were going to say they came back with "21 неделя вес набрала 20 кг singfinance info/]singfinance нефрология детская вакансия
футбольный клуб арсенал eurolegislation info/]eurolegislation info/ тайна богов Вербер
Третья глоабальная научная революция xcomputerz info/]xcomputerz info/ auto jet 100 l"
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