Brakes from the ground up Actuator/Booster

Hello Everyone,

First time poster here looking for a bit of guidance I've got a few things already including posts from this very forum but wanted to see if anyone could confirm a few things.

For Context/Backstory, My kiddo had been looking for a car, we found a gen 3 prius at a pretty good price point leaving him with a bit of extra cash for repairs. Initially I thought this thing might just need a Brake job and call it good but as we dug deeper we found it would be better to replace a few things to be safe not sorry down the line. That said here is an entire list of what we have identified as needing replaced and are in the process of doing.

Hubs - Front and Rear -
Abs sensors - Front(Rear are in the hub)
Rotors
Pads
Calpier Slider Pins and boots
Caliper Piston rebuild.
Brake Acctuator
Brake Booster

While the Hubs, Sensors, Rotors and Pads are fairly easy and straight forward I'm having a bit of trouble with the boots for the parking brake but am hunting down some long nose snap ring pliers to get this handled.

That said I've got the Calpier most of the way back together excluding the boots for the parking assembly, Herein comes my first question. I am hoping to entirely bleed the system since I am going to replace the booster and acctuator anyway. Would it be best to bleed it dry before installing the new ones?

Should I fill the Caliper with Brake Fluid before reattaching it or would I do this after the bleed?

At this point I'm weighing replacing the lines as well as it would probably be more straight forward but I did not rebuild the front calipers so I am on the fence about it.

Any advice anyone can provide would be appreciated.

NOTE: We are also moving to Dot 4 Brake Fluid from whatever was in there.

I've previously seen this video in a thread but if anyone has any advice regarding the bleed I would appreciate it greatly.