Upgrading windows 7 Pro to windows 10 Pro MS 2012 R2 Essential


I’m a system administrator in the IT Department. And still, now I’m working for upgrading 5 desktops to Windows 10 PRO from Windows 7 PRO - Besides, we are connected to MS Server - 2012 R2 Essentials.

Our computers are from 2015 - and I have done the math regarding upgrading or purchasing new - and Upgrading is the best way to go as we are running a nice setup.

· System Models Dell OptiPlex 9020
· System Types x64-based PC
· Processor Intel® Core™ i7-4770 CPU @ 3.40GHz, 3401 Mhz, 4 Core(s), 8 Logical Processor(s)
· BIOS Version/Date Dell Inc. A25, 5/30/2019
· Hard Drive - Crucial MX500 SSD
· Memory - 32 GB

I’ve been managing all of our IT needs for some time - as our amazing IT prof passed away a few years ago - and I have yet to find a company that I want to work w/like most of the time I know more than the techs they send out (which is just enough to be dangerous). Besides, I installed the setup we have now - have no problem upgrading memory, hard drives, etc…

So, with that being said - I’m running into a few issues as I try and navigate my way through this upgrade before the EOL date…have tried finding some sort of step by step – as I am an accountant by trade – and like to do things methodically.

This is what I have done so far:
1 Ran Support Assist through dell and have all updates – BIOS, Drivers, etc.
2. Upgraded Memory to Max
3. Upgraded Hard drives to SSD
4. Cleaned all computers – internally -
5. Backups on Server and a separate external hard drive
6. System Images of ALL computers
7. Ran Belarc
8. Will disable/uninstall – Antivirus/malware

These are some of the questions I have:

  1. Should I upgrade or do a fresh install of Win 10 PRO?
    · Pros and Cons?
    · Will, I need to upgrade drivers again?
  2. Either way – can I purchase from a reseller – or should I go directly to MS?
    · Pros and Cons?
  3. Will I need to reconnect my computers to my server?
    · If I do – will I just use the Connection Software as I did w/Win 7
  4. Can I upgrade the memory in my Server –It’s a 2015 Power Edge T110 II – 8 GB 1600 2Rx8, 4G DDR3L – w/an Intel Xeon E3-1220v2 3.10 GHz

Turbo Quad Core/4T
· If yes – what is the max amount
· Are there any videos? Having a hard time finding info on this…

A couple of my concerns as of now:

  1. We are running one computer w/Win 10 pro on it now – and shows unavailable – I believe this happened after the recent updates – I found some documentation that it was an ongoing problem w/updates in general

  2. Am I missing anything?
    I plan to update one that is not used as much first – then go from there –
    There is not a lot on these computers except mine – we use MS office 365 – so that part will be easy as far as email, word, excel, etc. –(hopefully) I think my biggest concern is not being able to connect to the desktops thru the server – I use RDP to manage them now.

Thanks for any advice on Best Practices as we update – and possible links to a step by step list and videos that pertain to what I am trying to accomplish.