UPDATE TIME:
TL&DR
I’m going to use a Surface Pro 8 for my law practice and iPad Pro 11 for family and fun (communications and hobbies).
The LONG Story
iPad Will Eventually Win: I’ve been using the beta of iPadOS 16 since June 8 (the developer beta 1) - not full time but on an experimental basis as much as I could. For me, and my workflow, the new iPadOS 16 paradigm is a long way from making this my ONLY computing device. However, it will still be my long term choice for a single computing device as I get close to retirement in a few years (more on this below).
Stage Manager: Make no mistake, iPadOS 16 is a big improvement in M1 iPad usability thanks to Stage Manager (multi-windows) and true external display support. (one monitor up to 6k). The issue is that rather than adopting MacOS window management, Apple is threading the needle (a very SMALL eyed needle) between classic iPad functionality and a “touch first” multi-window design. This is very buggy still on an external display, but is working on the iPad Pro 11 itself. In a nutshell, Apple decides placement, size, and stacking of your allowed four windows. They focus on the most active window, which generally gets “center stage” on your device, with your other windows stacked behind the center stage but at least partially visible for selecting and bringing forward. You cannot force a window to stay in the place, or size, that you select and routinely it shrinks/moves all your windows in this stacked overlapping arrangement that it decides. It can be disorienting when you move a window in upper right corner and everything reshuffles back to an invisible grid of Apple’s design. For casual use, or even heavy duty photo/video editing, this is ok, but it is a headache for productivity focused uses, ESPECIALLY on an external monitor, where the window behavior is the same. I have sent many messages to the beta team that they need to be more Mac-like for window management on an external display - no response. I’m not the ONLY user complainign about this, but this really feels like the epitome of Apple’s “we know what is best for you” moments.
File Management: The Files App is much better, but it is still NOT a Finder or File Explorer replacement, not even close. I think this is because you still can’t really create a file structure locally on your iPad that apps can access - they can only access files created or used by the specific app and stored by it - or cloud stored files (iCloud, OneDrive, Dropbox). The upshot - my file structure is client/project driven, so if I am analyzing a contract, all document types for that contract are in one folder - the Word version of the document draft(s), Excel financial analysis sheets, PDF attachments, JPG’s of equipment or real property, etc. I can’t be bothered to “share” a specific file to a specific app - and likewise when I do “File Open” in Word and see a pdf I also need to look at - I want to right click and open in Adobe Acrobat…get my drift?
MacBook Pro 14: This is the best laptop I have ever owned, and works in tandem with all my other Apple gear, but in effect I am using it like a Windows laptop replacement to do the functions described above, only “in the Apple way.” In effect, it becomes the odd man out in my workflow.
Surface Pro 8: Which brings me full circle back to where I was four months ago - business is “Windows-like” and personal is “Apple-like” and the Surface Pro 8 gives me a more complete business solution thanks to the touch/pen interface that MBP14 lacks (without a second device - the iPP11). Example:
I setup a used SP8 attached to my TB4 hub and two external monitors. Then I interviewed a client about some answers to interrogatories (written questions you answer under oath like a deposition) with very easily took notes on the SP8 in draw mode, while having three different Word docs and my calendar open on my two 32" 4k monitors. It was so much easier than juggling the MBP14 and iPad, in two different OS modes, to accomplish the same thing.
Bifurcation: Basically, I’m weary of juggling OS’s and hardware all the time, especially to make my business life work with my desire for “Apple things.” As a good friend here pointed out (very strongly) that since I still need to make bread, I should use a proper oven rather than trying to pan fry a loaf. I’m at least 3-5 years from full time retirement, so I’m going forward with Windows (SP8) for my business life and iPad/iPhone/Watch for my personal life…simple, right?
Until the next turn in my saga…