> I had thought Xilinx ISE and Altera Quartus had the market cornered on the most difficult environments to get running, …
These tools were the reason why I gave up on FPGAs years ago and chose to spend my time on GPUs instead. And to this day, I still don't understand why they worked so differently from what I had expected in so many ways.
I highly recommend getting a small, cheap FPGA development board with something supported by Yosys, like a Latice ICE40UP5k, Efinix T8F81C2, or GOWIN GW1NR-9.
Yosys is a super lightweight open-source FPGA toolchain that really easy to get up and running. The FPGA models I mentioned have ~5k to ~10k LUTs, can all support simple RISC-V processors, and have built-in memory and DSPs.