Finally got a mostly-functional version boxed up. The headphone amp sounded better on the breadboard, so I'll have to take a closer look at that. I haven't soldered the dummy load in as I wanted to test everything else first before I really commit to it. Plus I needed a dry fit to make sure I could get everything into a 1590BB

So it now has a single input for guitar or amp, a 4/8/16 ohm dummy load that can be bypassed for either using an external cab or for plugging a guitar straight in (the DPDT switch), a gain control on the input of the speakersim, and a headphone level control. The three outputs are speaker out, line out, and headphone out. I don't have the dummy loads wired in yet, I just put them in for a dry fit and I'll solder them once I finish thoroughly testing everything.
The rectangle holes for the displays were milled with my CNC, but you can see the left one had some issues and the right one came out much cleaner. This picture was taken before the jacks were mounted.

And this is how it looks right now with the 100W power resistors in place. It's a little tight in the 1590BB, but it fits

