Hi there
You almost answered the question yourself - the answer lies in question 3
Which version of windows would the user be purchasing - OEM or Retail
The main differences between the two is that with an OEM version the licence is NOT transferable to another machine. The serial is tied into the system by the motherboard. Any major change in hardware will invalidate the licence. Also OEM versions are not intended for general retail. They are for system builders only, at one time you had to buy hardware in order to purchase an OEM, most people got around this by purchasing a mouse at the same time. No software support comes with OEM's by the way of Microsoft, it is up to the system builder to provide any support for the software.
A retail version is a different in that you can transfer the operating system across to a different system, but you must only be installed on one machine at any time, once you have installed the operating system on the new computer it must be removed from the old computer. Retail version also tend to come in a nice fancy box, unlike the OEM version which usually comes in a plain sleeve. You also get full support from Microsoft for the operating system.
Another big difference between the two is the price. Usually the retail version can cost over twice as much as an OEM. What I would say is to look at what offers Microsoft have running regarding the retail version. Normally it is cheaper to purchase OEM twice (once for each computer) rather than buying a retail version and transferring the licence. At the present Microsoft is pushing windows out with various offers, they had the pre release offer where the retail version of premium could be picked up for as little as £50, unfortunately this offer has expired and has moved up to its next pricing stage. Windows 7 premium is currently now on offer at £79.99 from Microsoft themselves. There is also the new students offer in the UK and in other other countries where Windows 7 can be picked up from £30. As far as I am aware the pricing for any OEM has not been released, but with the offers that around it may be beneficial to take advantage of them while they are around.
EDIT: Looks like Ian beat me to it while I was typing