Building the "Dream" pedalboard is extremely personal to what you want/need.

I am not going to give my opinion of what the "answers" to your questions should be, but will offer the following tips.

Having your tuner before the compressor can actually generate noise that the compressor will pick up and add to the mix.

I never have an "always on" selection, as they may not fit the sound you're looking for at whatever given moment.

I've found Strymon power supplies to be the best so far. The downside is they're pretty expensive.

Pedaltrain may make a board big enough to hold everything, but my personal preference is to have two boards. One is "general purpose and happy to take anywhere, including gigging", the other is "stereo and will probably never leave the house". Then there are a selection of separate pedals such as expression, volume and wah.

There is no ideal chain order. Also, midi will not alter the chain order, as all this does on a pedalboard is send control signals.

Unless you already own all the pedals in your list, I would suggest getting to know what you already have before adding your "perfect" next addition as you will probably change your mind several times along the way.

Be prepared to be disappointed from time to time.... a new addition to the ensemble may not give the result you were expecting/wanting.