I’m not sure where to start, especially since my pre-pandemic workflows have faded a bit from memory. For many years, I was the sole Mac user in a PC-based firm, but I also kept a Windows machine running in my office. My happiest moment was about four or five years ago, when we switched from document management and case management systems that we hosted in our server room, and required Windows locally, to cloud-based systems. That allowed me to get rid of the Windows machine and go 100% Mac.
Drafts might be my most essential piece of software. In most meetings, I type notes in Drafts on the iPad, which syncs over to Drafts on my iMac. And when I’m at my desk, notes from almost every new phone call or thought goes into Drafts, before getting transferred into our case management system. I have various Keyboard Maestro macros and text expansion snippets to help with this. For example, I have a Typinator snippet that sets up a template if I am talking to a new client, and then I have a Keyboard Maestro macro that converts the Markdown headers to the kind supported by our case management system. I also use the keyboard shortcut to call up a new Drafts note wherever I am on the Mac.
DEVONthink is my repository for items that don’t go into our case management system (common legal research that spans cases, administrative documents for the firm, etc.), but I also mirror select cases locally to DEVONthink for trial, depositions, etc. That gives me quick access to everything, and lets me use the power of DEVONthink’s search, etc.
To answer your question about Hazel, I don’t use it nearly as much as I did in the past. DEVONthink has smart rules that can be applied to imported documents, so I find many of my rules have moved there. I do have a Hazel rule that detects when I’ve downloaded a document from our case management system, and opens it in the default app.
This is getting a bit long, so the final thing I’ll add is that I’ve programmed buttons on the Stream Deck, using Keyboard Maestro macros, to filter notes in our case management system by various tags. This lets me just tap a button to get to desired notes.
On a side note, ironically, at the start of the pandemic, we bought MacBook Airs for our entire staff, and there was some grumbling about learning something new. But as people are returning to the office, I’m hearing grumbling about getting back to Windows now.