Figure out what you have to get done first. Try the basic stuff and don’t add anything until you have to. I’ve been using Macs since the original 128K Mac and I have to confess that I still don’t use Alfred, or Keyboard Maestro.
Now I do use Hazel, and am expanding that. And I tend to pick the more complex packages for the other tasks I use so I use DEVONThink, Scrivener, Omnifocus, LightRoom Desktop, Photoshop, Carbon Copy Cloner, Aeon Timeline, 1Password Standalone version and LibreOffice.
We are a no Microsoft house entirely here. But I’ve found so many issues with sharing Pages, Numbers and Keynote with others that I’d go instead with LibreOffice. Free and still allows you to open and save in MS Office formats if required.
Get used to the new system and your uses and then pick software if you need to for additional or expanded uses.
As @Topre says, most Mac software comes with a free trial so when you run off the end or have a need, try several options to see what fits for you.
I’d recommend Keyboard Maestro as it is easy to learn and extremely powerful. It also covers what lots of smaller utilities do, for example, Text Expander and Hazel, and has a low one-off cost.
Spotlight (the default Mac search) is extremely capable, and I recommend using it and seeing if it fits your needs before trying Alfred or LaunchBar. I’ve tried both and have ended up just using Spotlight because it covers everything I need.
DEVONthink is fantastic if you need to store reference materials and want to clip websites. I use it as per the GTD method for ticklers and as a reference repository, as well as for scanning and OCRing documents. I find it to be just about my most used tool.
You can also save a lot of money by using software like Affinity Photo instead of subscribing to Adobe Cloud (a one-off €50 compared to about €150 a year).
Office 365 is one of the best performing and modern software suites, Microsoft has done a fantastic job in improving it over the years. You don’t need a VM for this at all. I’ve tried using other alternatives (Libre/Open Office and Apple’s office suite), and neither export well, at least not if you need to collaborate with others. They’ve also added features so can edit in real-time like Google Docs, and it works well cross-platform. Access is sadly not an option, and there’s nothing as good that I’ve found on Mac. The closest I’ve seen is Airtable, but it cannot connect to business databases in the same way that Access can.
@OogieM I have LibreOffice loaded and have tried it out I haven’t tried to share it or anything but I keep it there in case I need to use a Word compatible doc at short notice. It is reassuring to know power users use it succesfully. Are there any issues it might be helpful for me to know about?
Only the standard issue of differences in how Excel vs everyone else calculates dates. If you have spreadsheets that use date formats or do any calculations on dates you’ll have to set the proper start date in the LibreOffice preferences.