Mobile Device Management software to keep track of what’s installed on devices (probably won’t work with DOS)
I personally use a password manager to keep track of software keys, but realistically you should probably look for a way to get licenses that doesn’t involve typing a key everywhere.
MD is a great idea to promote during this transition.
I've found you also need a company system that is independent of system management tools - some places use a help desk ticketing system, some use a change management system.
Some friends in the SMB space use a single system for their company (IT consulting firms) to track their clients, client hardware purchase dates, contracts, warranty, every change they make, Admin accounts, device ID's, their billable time, etc.
This way all info on a client is maintained in a single place in case (this is the important bit) you get hit by a bus.
That's a common refrain - "what happens if bob gets hit by a bus?". Can't have any knowledge dependent upon a single person, everything needs to be maintained in a single, accessible form, hosted on company servers and backed up.
Being a small operation, this could be a hard sell. Maybe an open-source help desk solution that you can host internally would be acceptible. The hardest part with that is defining roles and who has access to what.
Something you may consider - small orgs have difficulty documenting their systems (basically it's a lack of manpower, you got shit to do, and documentation seems unimportant). Since there's a transition, it would be incredibly useful to introduce requirements gathering and documentation. A typical model defines Business Requirements, which are mapped to System Requirements, which are then mapped to Technical Requirements (e.g. One Business Requirement will often map to several System Requirements, which usually map to multiple Technical Requirements).
Look into Business Systems Analysis, there's some intro docs out there for how to do this, it's pretty straightforward, and you don't have to do all the detail, just having some documentation is better than none.
Documentation is non-existent now and that's what bothers me the most. I, at least, started to put my agenda and acquired how-tos to plain txt files for future, because with so much shit going on I tend to forget stuff. I'd like to extend it and make it system-wide to cover all the IT related stuff in the company with some proper software to do it in (no idea which). But there's virtually no way this lack of documentation will change dramatically anytime soon. There's simply no will from higher ups and even if there was, there would be no manpower to do it :-( We're barely holding things running.
Here's an idea, since you're an MS shop - OneNote.
My SMB consultant friends use it as a secondary, shared, more comprehensive and free-form way to track system docs, changes, etc.
It's so easy to use, just using it yourself will sell it to other people in the company, besides giving you a single place to store stuff (that can easily be shared or copied elsewhere when needed).
When someone asks "where's this" and you can pull it up in seconds in OneNote, they'll be impressed.
Just don't use the Universal app version of OneNote, or use OneDrive - use the full version included with Office. I'm still using OneNote 2016,though I think there's a 2022 version (I keep all notebooks in the 2016 version just in case)
Store your OneNote files on a file share (that gets backed up, and that you can control access), so it only syncs locally. You won't get mobile device sync this way, but it never leaves the premises, and it's not sensitive to OneDrive issues (I've seen OneDrive hose a notebook). (You can do mobile device sync if you store notebooks on a SharePoint server).
I have a personal notebook I work from, plus a work notebook (which is just mine, not shared). I then create other notebooks as needed - I have an IT Reference notebook with saved web pages and docs of how to fix problems. My personal notebook has a section for a current laptop rebuild, with a spreadsheet embedded that I open every day to track changes and problems.
OneNote auto syncs between all devices using a given notebook. You can copy anything into it, even zip files or executables (don't do this, since OneNote keeps 3 copies of a notebook locally - working version, cache, and backup).
Last year I started using the PARA model for my notebooks, and it's a huge help with business stuff: one notebook with section groups (Tabs) for Projects, Area of responsibility, Resources, Archive. I've added a fifth section, Reference, to my work notebook.
I do things like share emails from outlook to OneNote - it puts the email in there with all it's info, then I can add notes as needed for reference. Great for tracking Approvals.
If you start using OneNote, there are numerous paid and free add-ons for it that really extend its ability to sort, search, layout, edit, etc, such as OneMore and NoteGem. Just the calendar showing notebook changes is worth installing either one, but the section and page sorting is a massive help.
I have 15 years of nitebooksbat this point - be judicious in setting up and organizing your notebooks. I've found the idea of Archiving to be hugely helpful.