Multiple windows open

As we are now on Windows 64 bit not MSDOS 16bit why is it not possible to have multiple windows open at the same time. I am forever having to switch between windows closing then opening and then closing, opening etc. I have even resorted to writing things down on paper so I dont have to keep doing this which seems really retrograde.

Also how do you rest a cyclist? - it seems logical to have a 'rest' checkbox some where but I cant find one, so how do you rest a cyclist?