I didn't think about 1, that actually seems like a really good idea! I actually found yet another method in the meantime, schedule a flight loop source that reloads all plugins, that way I can completely attach everything I need. It's super clumsy though.
#1 is definitely the best option I think, because quite frankly I'm lazy and I would love it if my IDE could just automatically attach the debugger for me instead of doing it manually, so it's easiest if I can point the IDE to the x-plane.exe directly. I guess eventually I'll bite the bullet and buy X-Plane again since I'll need joysticks for longer than 15 minutes at some point (and by need I mean, I would rather gauge my eyes out than play X-Plane with a keyboard)