Windows to macOS conversion

Apologies if I've selected the wrong forum; this is my first post here.
I'm planning the conversion of my mature Windows installation to macOS. A summary of my conversion plan is attached below.
Any comments or advice will be very much appreciated.

Conversion Plan Summary
Objective: Convert a mature Windows 7 installation to macOS.
The user: Retired systems and network manager. Early experience with Apple Lisa with MacWorks and Macintosh Plus with HD20; twenty-five years with Microsoft Windows from Windows 3.0 through Windows 7. Current experience with iPhone 6S Plus.
The installation: Three Windows 7 systems on a secure, private LAN. Storage includes twenty-five year archive of personal files including financial records, correspondence, digital images, music and miscellaneous documents of all kinds. Substantial commitment to Outlook 2003 POP3 e-mail client, Calendar and Task Manager, Word, Excel, Quicken and Photoshop.
The philosophy: Build a macOS installation to provide functionality similar to the existing Windows 7 installation. Key to the conversion is NOT to match application for application but to implement the required functionality.
The plan: Install a Mac mini of sufficient capacity to be run side by side with the main Windows 7 system. This should allow the two systems to share an exiting 27 inch monitor through an HDMI switch, to share files across the network and to provide a backup facility for the Mac using existing (but not shared) USB-3 external drives. Conversion can then be managed at a comfortable pace, function by function, until the Windows 7 system(s) are no longer needed.

Welcome to the forum.

Your plan is good, but at a fairly high level. When you get the Mac and fire it up for the first time, it will take you through some welcome screens, select language/location, etc., and at some point will offer to migrate your data from another computer. At that point, if you point to the Windows 7 system you want to migrate from, it will let you move the files. I you'll need to get the migration application for Windows to put on the Windows machine. Here is a link: https://support.apple.com/kb/DL1557?locale=en_US

If you choose that time to migrate, then when you are done, there will be an account on the Mac that has the same name and password as your Windows system and all of the useable data will have been moved. NO applications move because none of the Windows Applications will run on a Mac under macOS. But your data files will be there (documents, pictures, spreadsheets, etc.). That is the easiest way to move most of what you want.

As for applications, you'll need to look for what you want. Office from Microsoft runs on a Mac, so Word/Excel/Powerpoint/Outlook are (sort of) the same. As for backup, there is a built in backup system on macOS called Time Machine that makes a full backup the first time, then incremental backups every hour by default. That should get you started. The backup drive for TM will require reformatting to the MacOS format, so prepare for that by migrating any files you want to keep off the designated drive first, then attach to the Mac and use Disk Utility to format it for Mac.

Other applications may or may not have Mac equivalent. If you let us know what they are, someone here can probably tell you what the equivalent is.

One more thing. MacOS cannot natively write to a Windows formatted drive (NTFS), although it can read from those drives. There are a couple of options to you: You can reformat any such drive to FAT32 which is read/write for both Windows and macOS or you can get a third party driver to allow writes to NTFS. If you go this third party way, the driver recommended here is ParagonNTFS, which I use and which is pretty good.

It's been a while since I made the move, so I don't remember how I moved the email. I seem to recall exporting from Outlook to .pst files an then importing, but don't quote me on that and it's been long enough that the process is probably changed anyway.

Photoshop, depending on the version, may be movable to the Mac, if you can talk Adobe into allowing you to do that. They allowed me to move my Mac version to a Windows version when a very old, but key, printer didn't keep up with Macs and forced me to a Win7 system (Virtual on my Mac). But they sternly warned that it was a "favor" and that moving back was strictly forbidden. Good luck with that one. You will need, if they allow it, to unregister the Windows version before you can re-register the Mac version. The Adobe Mothership is very stern on that!

Welcome to the world of Mac. It's different, so don't expect it to be like Windows. You'll love having no need for antivirus because there aren't any, but you will need to be open-minded about how things work. In the long run, I've never regretted my own migration 10 years ago.

EDIT: PS, if you DON'T migrate when the first offer comes in, it can still be done, but is much more labor intensive later on. The very next step after migration, if you don't do it, is to establish your own new account, and at that point the OS will be careful not to allow migration assistant to write to YOUR folders. So you'll end up migrating, then having to find and move the files to your account and then do some more gyrations to change permissions (security) to allow your new account to write to the old files. If you migrate earlier, then the account will have ownership of the migrated files and you won't have to do that work. It's your call, folks have used both ways successfully.

Thanks for your help and for your interest in my situation. My intention with this first high level post was to look for some encouragement that I wasn't heading off in entirely the wrong direction. As the process moves forward I expect I will benefit from additional, more specific advice.

When I mentioned a 'comfortable pace' for the conversion, I expect to still be supporting at least some of my requirements on the Windows 7 platform for a year or more. Data will only be moved when the related functionality has been implemented on the new platform.

A major advantage of this side by side approach is the ability to 'try it and see' when looking for solutions. And I should mention that my escape from the PC platform is not just from Windows but from Microsoft in total. Accordingly, I will not use Office. Also I may exercise some bias in favor of native Apple software.

Since I plan to replace functionality, not applications, the functionality now provided by Office may be served by more than one solution on the Mac. For example, I've already begun tinkering with Apple's Mail program on my iPhone and I'll probably try others like Pages, Numbers and so on. And there're other suites like Libre etc, etc.

Backup is a first priority. I'll probably start with Time Machine and look for something more robust if necessary.

Disk sharing between Mac and PC will be limited to copying PC files to the Mac as required so I should be OK with just the Mac ability to read NTFS.

Thanks again and you can be sure you'll see me here again. Who knows - maybe someone else might benefit from my experience.

Well, there are two ways to go to Mac. The slow, gentle way you are suggesting and the "jump in the deep end" commitment approach. I took the latter about eight years ago. The shock was large, but the learning was much faster than I think it would have been the slow, gentle way. The reason is that by having JUST the Mac, I had to learn how to use it to get things done. The two systems are different, and you need to think differently when you use one or the other. One way to maybe make a hybrid approach is to get an emulator like Parallels or VMWare and run Windows in a virtual machine on the Mac instead of keeping the Windows hardware. That way you are actually USING the Mac, but still have the Windows environment. I am pretty sure Parallels still has an application for Windows that will create a virtual machine of your Windows box, which can then be run on the Mac exactly as it is on the PC, just in a window. I have parallels to run Windows for a printer driver for an old, but critical, printer for my wife's business. They didn't update the driver for Mac past a couple of versions ago and haven't updated the Windows driver since Win7, so I bought Windows and installed it in a VM, then installed the printer driver and migrated my Mac version of Photoshop to the Windows VM with permission from Adobe and have that virtual system only for when she needs labels printed on that old label printer.

Comparing functional side-by-side will almost always be unsatisfying. There will be things you can do in the Windows version that the developers have NOT moved to the Mac version, and vice-versa. Depending on how much you rely on the things that are hard, or impossible, to do on the Mac, you may never finish the slow process, always hanging on to that "favorite" thing in Windows.

Finally, while you can certainly leave MS behind for all time, there is no reason to HAVE to do that. I have Office365 and use Word, Powerpoint and Outlook for an organization for which I volunteer so that file compatibility is assured. They actually run very well on my Mac and I am very pleased with having them. So unless you are leaving behind MS for a philosophical reason, there is no practical reason to have to do so. I still use the Mac Mail system for my personal mail, just use Outlook to get to the organization's email server smoothly. And while Pages, Numbers and Keynote are mostly compatible in that they can open Office files and export to Office format, sometimes moving files from Office to them and back to Office loses formatting, or fonts, or something, in the transition. Just be aware of that if you share files with Office users.

Thanks for your advice. What you say is true and well considered. During my forty years career in network and systems management I directed several large scale conversions of information technology. In those days, the "jump in the deep end" approach you described was known as a "push/pull" installation. Push out the old stuff and pull in the new. I like your name for it and you're right - it sharply increases the slope of the learning curve.

But I'm retired now and I enjoy the luxury of setting a more leisurely pace. The deep end was obviously the best approach for you but, absent any compelling reasons to work under pressure, I think I'll still prefer to take it a little slower.

And by the way, my reason for leaving MS behind is both philosophical and profound. With its recent campaign to force the Windows 10 upgrade on users by any means, against their will and, for many, even without notice, Microsoft had become the single greatest threat to the security and integrity of my installation. For my own safety, Microsoft is now and forever denied access of any kind to any of my systems.

Thanks again.