The number of pedals you plug on 1 output is irrelevant as long as the combined current draw does not exceed the current supplied by the output.
If you overload an output, some pedals might not work correctly or might not even turn on and the ISO-5 could also shut down (it is purposely designed to do so).
If you daisy chain several pedals on one output, you will lose the benefit of isolating them from one another. Pedals will now have contact with ground through the signal cables and through the power cables. It opens the door to possible ground loop (hum/noise). Before crying wolf it does not hurt to try, it might work seamlessly too, it’s difficult to predict.
The highest current output on the ISO-5 is 300mA and not 400mA.
From the latest pic of the pedalboard you posted, I can see you have:
- Boss DD-2: 55mA
- Boss PH-1r: 11mA
- Boss RV-3: 70mA
- Boss Tu-3: 30mA (85mA in high brightness mode)
- Blackout Effectors Mantra: From builder website <50mA (I suspect it draws much less)
- Blackout Effectors Musket: 10mA
- Blackout Effectors Whetstone: 45mA
(55+11+70+30+10+45+50)=271mA
There are many ways to power this lot from your ISO-5:
You could daisy chain all these pedals from the 9V – 300mA output which would free all the other outputs*.
You could use couplers or Y cables and daisy chain some of these pedals 2 by 2 on different outputs.
Note also that the Blackout effectors effects can all be powered with more than 9V. So it might be interesting to have the Mantra and the Whetstone on a coupler powered from the 18V output (100mA max) for instance. This in turn would also free some space on the other outputs.
You could daisy chain all the low current draw pedals on the same 9V – 100mA output: PH-1r + Musket + Tu-3, etc.
*This is partially true, the 12V output could not really be used anymore. The combined output of the 9V output and the 12V output labelled 300mA should not exceed 300mA. They
work together (well it could still power 1 low current draw pedal @12V)