is 8GB enough for iOS dev and occasional VM? I'm going to buy a rMBP 13'' (i5, 256gb) exclusively for iOS\OSX development. I might run a windows VM occasionally (visual studio).

I plan on keeping it for ~2-3 years.

Should I go for the default 8GB ram, or is the $270 (that's how much it costs here) upgrade to 16GB ram worth it (in my situation)?
According to Visual Studio's system requirements, it requires 1.5GB when in VM.
Usually you will assign a max of 4GB on the windows VM which should be sufficient for a satisfactory operation of Windows inside the VM with the Visual Studio. 

In this case there will be 4GB left for the hosting OS. Which usually is again adequate. 

Also, Yosemite does a really good job in handling CPU and Ram, so in my opinion you should be ok.

My personal experience with a 2009 MBpro, 8GB Ram on Yosemite running windows on VM shows that there are very rare the occasions where I am out of RAM.