I own a 2013 13" Macbook Pro and currently use a 2017 13" Macbook Pro at work, and I like the 2017 better.

The only gripes I have with the 2017 machine are the butterfly keyboard (which never broke, but just doesn't feel good), the lack of an ESC key, and the "space grey" color.

From trying out a 2020 13", the new keyboard actually feels like an improvement over the 2013 one, so I guess that's fixed. It has a physical ESC key, so that's fixed too, and ... there's always the silver model, but my employer couldn't procure that at the time, and I guess it's not such a big deal really; I just like shiny things I guess.

On the upside: I can get a tiny machine with 32GB RAM now with a UNIX on it that doesn't require me to be my own Linux sysadmin, which is something I know fairly well how to do (I do admin a number of servers, and have had at least a dozen forays into Linux on desktops) but absolutely don't enjoy to the point where I'd rather use Windows 8.

Besides, Touch ID is something I've grown to miss on the 2013 one, since I hate typing long passwords over and over again, and it even works for 1Password and apparently is reasonably safe at that.

I have a 34" USB-C screen, which makes USB-C a really nice experience; single wire and I get display, a couple of USB devices (including my mechanical keyboard), LAN access, sound and power. Everything works out of the box, no issues so far with the 2017 Macbook. On the 2013 one, I had to use three cables for that (those Thunderbolt 2 docks never felt like good value for the money) and it turns out USB 3.0 does have its limitations.

I even like the touchbar. I'm fairly disinterested in peak keyboard speed and efficiency, I don't need a debugger that often really, and I'm bad at memorizing keyboard shortcuts anyway, so I like being able to get a discoverable set of shortcuts on the touchbar. Setting brightness and volume has a lot more granularity, that's nice too. I have a button to mute my microphone on there as well that shows the current muteness state, useful for conference calls in Teams (its mute shortcut is weird, plus this way I don't show up as muted, which is better sometimes) and I look forward to trying out BetterTouchTool. I've seen other people use theirs as some kind of makeshift faders and fairly precise "analog" sliders for image processing and the like – not quite as nice as having dedicated devices for it, sure, but it's always there. I thought I'd hate it since the overall tone in the developer community towards the touchbar is incredibly negative, but I'm fine with it and I would pick the touchbar version over a F-key one any day even at modest cost (but I need the ESC key; leaving that out actually did make a difference for me.)

Haven't tried Catalina yet myself, but most of an office full of devs seemingly didn't have much trouble with it (the rest has yet to switch), so I guess I'll see what I find when I upgrade; I'm backing up my email just in case. But in the end it's probably still a UNIX that doesn't require me to become a hobby sysadmin and reboot after using the wrong projector, so I'll probably still be happier than with Linux, and somehow I just can't grow to like Windows.

That's just my personal experience, n=1 and all, and I don't use my machines to make music or develop in emacs all day at maximum keystroke throughput and so on, and I might hate the experience if I did, but as things stand, I'm currently still feel kinda positive towards Macbooks.