But if "conventional" EM waves are the subject, the line between microwaves and IR is 300GHz. How close have hobbyists been able to get to that line?
I don't fully agree that the line between microwaves (well, technically millimeter-waves at that point) and IR is 300 GHz, generally people would say that you have sub-THz first (300 GHz -> a few THz).
There are at least a few HAMs (WA1ZMS, W4WWQ, W2SZ, WA4RTS) that have done some stuff at those frequencies, 300-400 GHz. This was all with 'conventional' RF techniques (IE, no lasers or optics, but transistors and diodes and mixers).
While the numbers are impressive, it isn't that fundamentally different from RF at a few GHz. The main issue is just that *everything* matters, and you need to use waveguides or expensive very small PCB technologies.