Transmit high current with low voltage on a lightweight system

In general, a single boost circuit is preferable to using two boosters in series. I say this because, given the powers you require, a transformer is the most efficient way to do the step-up from 12V to 400V.

Not using a transformer will limit the power you can handle in stepping up the voltage. At these sorts of power levels you'd be hard-pushed to find a booster that doesn't use one. Once it is accepted that a transformer is a requirement, any turns ratio from a 100:1 (step-down) to 1:100 (step-up) is just a matter-of-fact (see comment below next paragraph).

Because a transformer is necessary to economically achieve the power output, the turns ratio is going to be an easily achievable 40:1. A 24Vp-p input at a frequency of (say) 10kHz will, under no-load conditions, produce an output of 960Vp-p which after rectification/smoothing is going to be about 475VDC.

But, high turns ratios and efficiencies don't always go hand-in-hand - I'm thinking of X-ray tube power supplies that I've used - they were 50KV/4mA output (200W). The step-up transformer was a large ferrite operating at 50kHz and, with about 1200 turns on the secondary you were starting to hit self-resonance. It was a resonant transformer circuit so that was no problem but more than 1200 turns and you were on the downward slope of decreasing efficiency. Input turns, from memory were about 6 so turns-ratio of about 1:200. The output fed a multi-stage cockcroft-walton voltage multiplier to take the output up from about 2000Vrms to 50kV.

More than likely (given the power), you'll need a H-bridge driver which will apply nearly 24Vp-p to your primary winding and the turns ratio will be 40:1 to produce +400VDC. It will need a reasonably sophisticated control system that involves pulse width modulating the drive to the primary and decent monitoring of the output to ensure you stay regulated. I would also say that a secondary shut-down circuit would be needed should a single-fault arise. Caution - fire hazard, electric shock hazard

Given the power supply's sophistication I'd be very hesitant to believe that two boosters would be at all more effective than one booster on the grounds of efficiency, performance, physical size or cost.

You need to get some spreadsheets going to understand your system.

Your chosen motors may well be capable of drawing 400A at low speeds. However, that doesn't mean they are drawing more power than when used at high speed, as the voltage will be lower. It also certainly doesn't mean you should be supplying 400A.

Your should look again at DC/DC converters. You need to limit, to control, the current into the motor at low speeds, in order to control your acceleration. A DC/DC converter will take your high battery voltage at low current and convert it to a low voltage at a higher current when the motors are at low speed.

If you simply slam in 400A per motor, I would expect the high torque to be able to spin wheels, which would waste energy and lose you control of the vehicle.

You do not need to connect all the motors in parallel, you could connect them in pairs and use a 1000A converter for each pair.

Your supercap 'solution' increases the weight and cost of the vehicle (probably bad) and doesn't solve the real problem, which is obtaining controllable acceleration from standstill.