I'm in a similar position.
I am running a 2008 Macbook Pro and it's struggling to even play a full screen 720p movie


.
I also do security so I need VMs, and I recently spun up a Win8 VM and it's literally unusable and its pushed back my studies a lot.
My predicament is buy now as it is, or wait until October or futher. Since Apple have upgraded the riMac in the past few weeks, I doubt it will be in October and more likely in 2016. I do not think I can really even wait until October to start studying again so I think when I get paid at the end of this month I will need to bite the bullet and just get the current one.
Skylake isn't a specific upgrade for me, I just need something faster, ability to add more RAM and just more generally up-to-date. I don't plan to use the screen in target mode/as another screen, but will be interested in buying another 27" screen as a second display, and I am aware thats what the current iMac can't do?
In addition, I am a console gamer, so I don't really need a souped up graphics card, but is there any value to me getting the best one for just normal use? Not sure if this will help the performance of the retina screen
The plan is:
-Highest CPU available (currently 4GHz)
-8GB RAM (Upgrade to 32GB via Crucial)
-512 SSD (Upgrade via Apple)
-Graphics card = ?
Anyway, going to take the next few weeks and WWDC to consider what to do.