I'll bite.
I started on ARMv5 back in the days of Sheevaplug/Dreamplug. At least that had JTAG, even if the cable did cost $70.
I have tried:
* Espressobin: While Marvell's hardware is pretty good, they've had trouble with the v7 board, resulting in the small community being somewhat bifurcated. I still don't think it runs a mainline kernel properly. At least the PCIe slot is standards-compliant. u-boot+ATF will always be a 2018 (?) Marvell fork, no one's ever going to update that.
* Firefly RK3399. Lol. https://lkml.org/lkml/2020/4/6/320. Although, if you can get ARM Trusted Firmware working it's a reasonably competent board.
* Vocore2. Support is reasonably helpful but insists that I use GCC 3.4.2 to compile the bootloader. Remember to back up the wifi calibration data - you can't ever get it back if you erase it. You will need to break out the magnet wire if you want to unbrick it. Shame, it's a nice little MIPS board.
* Anything Libreboard - use this, they've put a stunning amount of work in to get things upstreamed.
When I want to just work on something not on a PC, I keep coming back to the Pi. The Pi 4 is competent with an SSD attached over USB 3, and the Pi 0W is great for very simple tasks that need Linux. I wish it were better, I wish Broadcom was more open, but the Pi has the biggest community I've seen in any "hobbyist" ARM space.