Consider Adding an Active Buffer:
Since you're experiencing noticeable high rolloff and blocking distortion when using your pedal board in the effects loop, adding an active buffer could significantly improve your signal integrity. Buffers help maintain the strength of your signal over longer cable runs and can prevent high-frequency loss, which is often exacerbated by passive setups.
If your pedals have buffered bypass circuits, make sure to engage them, as they can also help
Doodle Jump maintain signal quality. However, if you're still facing issues, an external buffer pedal or an active buffer circuit installed in your amp could provide a more robust solution.