Tanenbaum's textbook is highly readable, comprehensive (surveys every major known solution to each major prpblem), and mostly correct. xv6 may be a smaller, more old-fashioned, and more practical approach. RISC-V makes the usually hairy and convoluted issues of paging and virtual memory seem simple. QEMU's GDB server, OpenOCD, JTAG, and SWD can greatly reduce the amount of time you waste wondering why things won't boot. Sigrok/Pulseview may greatly speed up your device driver debugging. But I haven't written an operating system beyond some simple cooperative task-switching code, so take this with a grain of salt.
Funny question since you bring up JTAG and RISC-V -- do you have a cheapish RISC-V device you'd recommend that actually exposes its JTAG? The Milk-V Duo S, Milk-V Jupiter, and Pine64 Oz64 all seem not to expose one; IIRC, the Jupiter even wires TDO as an input (on the other side of a logic level shifter)...
I don't know what to recommend there. I have no relevant experience, because all my RISC-V hardware leaves unimplemented the privileged ISA, which is the part that RISC-V makes so much simpler. The unprivileged ISA is okay, but it's nothing to write home about, unless you want to implement a CPU instead of an OS.
