[In many cases, legacy applications are the sole reason for the continued use of Server 2003.] Those applications may themselves be unsupported at this point, the company that built them may be out of business or the in-house development team may have been disbanded. Any of those scenarios would make it difficult or even impossible to update the applications' code to run on a newer version of Windows Server. Complicating any move is the fact that many of those applications are 32-bit -- and have been kept on Windows Server 2003 for that reason -- and while Windows Server 2012 R2 offers a compatibility mode to run such applications, it's not foolproof.
What's the gist on all this? How much of this stuff is potential malware? What are your experiences? Can I usually trust rooting strategies to be malware-free? Is there a rule-of-thumb for this? Is there perhaps a more generic way for a FOSS/Linux expert who isn't afraid of the CLI to root any Android 4.4 (Kitkat) device? Advice and own experiences, please.
It's fine if the documentation is highly technical, I've written linux kernel drivers before :)