Hello everybody. I am a systems administrator for a real-estate and development company in the Buffalo, NY area. Between corporate office and the other 7 off-site locals I manager around 100 internal workstations as well as agent-owned devices (laptops, tablets, mobile devices). We utilize Windows Server 2008 RT to manage our file, print, antivirus, mail and active directory servers. We also utilize a SQL server for our databases using a program by the name of Yardi. Things have been running rather smoothly although I've own been working for the company for 4.5 months. That is my entire career in IT thus far as just becoming a graduate with my Bachelor's Degree. I run the entire IT department myself because the director of IT had unexpectedly resigned.

This question is more of an inquiry for advice down the road. When is it suitable for myself to upgrade our servers to say Windows Server 2012? 2008 is now 7 years ago and although things have been running correct when do I start to make that decision when our servers need an upgrade?

Any advice would be appreciated. Thank you.