I have just ordered a 16in MBP. I ordered the 2.4GHz 8-core i9, 32GB RAM, AMD with 8GB, and 1TB SSD. I figure this will meet my critical need to update yet also give greater future confidence that I can run Windows in Parallel when needed. My current mid-2013 MBP certainly shows its age with dents and scratches (and marks on the screen glass). I am still on Mojave. I look forward to Catalina with SideCar for my iPad. OTOH, at least one app that I have may have some issues in transition. We shall see.
I plan to re-install every app from the ground up rather than using the Time Machine approach. I prefer the tedious effort to the “easy but you will get old scruff” approach. I have a collection of the serial numbers and keys for the apps stored away for just this occasion. I have both a Time Machine backup and a CCC duplicate of my Documents to cover all the documents across my two login IDs.
As for additional hardware, I figure that I should be set with everything except the Thunderbolt/USB-C to USB-B transfers. I do ethernet through the thunderbolt, and I have adapters for thunderbolt to DVI, HDMI, and even VGA to handle the second monitor that I use, one each in each of three different locations. I have a lot of (legacy already?) USB-B hardware to interface. This includes especially an old Goldtouch keyboard and Kensington trackball as well as a collection of USB-3 external hard drives, one of which also interfaces through a USB to Firewire 800 adaptor. I carry this old stuff around because it still works. I imagine that I will simply purchase a USB-C to USB-B (hub input) transition cable and run everything off of the USB-B multi-socket (and externally powered) hubs that I use. I see no reason to get new hub hardware here. I’m not in serious need of getting thunderbolt speeds on any of the peripherals (e.g. I don’t touch type that fast ;-)).
Once I can be certain that the new machine is running in the same way as my current machine, I’ll wipe the old MBP and do a clean install of Catalina on it. The old machine will then be gifted to a family member who wants a portable to manage her photography work. I increased the RAM to 16GB and installed a Feather 1TB SSD in the old machine sometime ago, so she should be set for another 3-5 years with it.
In posting this, I heartily thank the many of you on this forum who have posted your experiences, insights, and comments about various aspects of the new 16in MBP as well as your thoughts about various upgrade paths from older machines. The posts are too numerous to assemble immediately. Each has in some way help me to build a bigger picture and become more confident in the purchase that I have just made.
Based on my experience with my 2013 MBP, I decided to order micro-fiber cloths that are to go over the keyboard when you close the shell as a way to protect the screen from oil and ding marks. I carry this around between home and work and travel, and I hope the cloth will mitigate against the occasional bumps through the travel case that might consequently compress the shells (and leave the ding marks on the glass that are now a hallmark of my 2013 MBP screen). In light duty, I also just use the tissue paper that comes with the original packing.
I transferred much of my setup from my 2013 MBP though external hard drives or through local internet sharing. I prefer this approach to Migration Assistant as a way to remove the accumulated clutter from the old machine. It does require additional levels of patience, for example to re-configure preference settings on apps so that they have the appearance that you are used to using.
I do notice a tendency for the computer to get warmer than what I remember from the 2013 MBP. I typically only have the power plugged into one port and an HDMI+USB-B+ethernet adaptor plugged into another port. I have lap stands/trays that have airflow fans underneath the MBP at my home and office, and I keep them running as I work.
I do like the touch bar and have installed Better Touch Tool as a way to invoke actions. I don’t like / cannot yet get used to the change that has been made (from Mojave to Catalina) in the sensitivity of the track pad to be able to grab a file or folder to drag it to a new location. And while the trackpad is bigger, I occasionally end up inadvertently touching it in the corners while I am typing only to find that this selects and deletes sections of my text.
Already my space bar is showing a worn-spot from where my right thumb hits to type a space.
In summary, I am glad that I got the 16in MBP now rather than waiting for some future discount on it due to a release of the first ARM Macs.