Cool way to connect two amps preventing groundloop hum. Use two PASSIVE DI-boxes for this.
As you can see, one passive DI is used in reverse position. (passive DIs are needed for this). This same trick makes a passive DI suitable as a re-amp box. (passive DIs often are cheaper then dedicated reamp-boxes)
How to hook up a guitar pedal chain to you DAW
1st DI box used in reverse to convert low impedance line level to Hi-Z guitar signal. You’ll probably need a XLR female-female converter to use the DI box’ XLR socket which normally acts as an output.
Use one of the DI’s instrument inputs as an output > guitarpedal input.
2nd DI will be used regularly Pedal out > DI instrument in > XLR out > make up gain stage. A standard line or mic preamp can be used as a gain makup stage.
The other way: how to include your DAW FX into your guitar pedal chain:
A Boss LS2, line selector, is used for dry/wet amount
Nice feedback loop with volume expression pedal as a feedback regulator: