Dear Spiceheads,
Long time reader first time poster! So far, I have accumulated so much experience from the discussions in the community but now I personally need your help.
(A little backstory so you can somehow "get" where I stand atm.)
2 years ago, I got my first big job in the company that I still am as the solo IT guy for a 95 personnel company. Every single co-worker has ties to IT one way or another. After ~40 years since its establishment, I am the first inhouse IT. So you can understand the situation that I encountered when I first got here. Things haven't gotten really better, because the management likes to cut corners wherever possible just for the sake of not spending.
Onto the matter at hand. After about a year of "hunting" the best possible deal for upgrading the 2 core servers (DC and SQL), and after accepting the one deal...