I personally find it easier to look at things in terms of horsepower; especially since the compressor map's X axis is fairly directly relatable to hp simply by multiplying by 10. So in the above referenced example, spinning at 27,000 rpm and 5 psi, you'd be somewhere around 500 hp. That would indicate n/a hp of around 370 hp. Engine displacement literally doesn't matter. And yes, without modulating speed, it's likely you'd hit surge at 2000 engine rpm. But more importantly, you'd possibly hit uncontrollable detonation at 27,000 blower rpm and 2,000 engine rpm due to extreme cylinder pressure and erratic fill, resulting in severe engine damage. Torque isn't your friend. Torque breaks things. I've blown up pistons and split engine blocks due to too much low speed cylinder pressure in my positive displacement DIY blower setups (using both Eatons and Lysholm/Whipples).
That said, I'd first do the Castle/Hobbywing setup and then a VESC/Castle setup. I honestly wouldn't use a TP Power motor simply because of the pole count; but I might try also try a TP/Hobbywing combination. The VESC is really problematic at high eRPM and the day-to-day lack of repeatability really makes me question any sort of data it spits out - obviously, something's wrong with it, but it's not my prerogative to make their stuff work as intended. I purchased it as fit-for-purpose, and I think I've proved unequivocally (to myself anyway), that it isn't. I honestly don't even think it's the best choice for electric skateboards. People sometimes seem to have a hard time accepting that a product like VESC is flawed. That's where life experience and ability to set aside confirmation bias is imperative, especially after dropping $500 on something that doesn't work as promised. I simply don't look at it as $500 wasted, but rather $500 spent on learning that something doesn't work.
As for batteries, I'd personally look for two 6s packs to minimize connectors, and I'd certainly not hesitate to use SMC lipos (or some other high-quality lipos, but I'm quite confident in recommending SMC stuff after my conversations with the owner of the company and his point of view on the industry - at least you'd be getting what you paid for.
I didn't use any sort of tensioner other than a slotted bolt mount to set the belt tension manually. Since it's a toothed belt with steel wires inside, it simply hasn't been necessary. I can't say the same for conventional serpentine belts in other applications.
Oh, and as for finding a smaller supercharger - yeah, that would be great, but I haven't found a reasonable smaller unit (price, availability and ease of application). Plus it's always better to have too big of a compressor rather than too small.
HTH.