Am I an idiot for wanting to boost a high compression 318?

Hi All, I have a 318 in a 1975 Duster with the following specs: 10.3:1 static compression, 4 barrel dual plane air gap intake, Clevite hydraulic flat cam w/226 duration and 0.453 valve lift, headers, edelbrock carb, stock bottom end, some head work I did on my own, and at 5200 ft in elevation. I estimate I have around 320 hp at the crank based on those fun online engine hp calculators. Here's what I want: I want the engine to be more reliable (I have been getting vapor lock in the summer) and I want 400 hp at the wheels and I want to do it in the easiest way possible (not the cheapest) and I do not want to run NOS. I have been looking at Holley's Sniper EFI system along with their hyper spark set-up to increase the reliability. For those extra horses I am considering a Paxton super charger. Again, not cheap (around $10K in total for both EFI and charger) but easier than rebuilding an engine or so I think ha. A few questions I have below:
  • Is this really stupid? I was thinking I could keep the boost pretty low maybe less than 4 PSI if I opt for a bigger pulley on the charger?
  • If I was running 4 PSI of max boost, what octane level would I need for this set-up? I am okay with using 91 and then mixing in something like torco to increase the octane level.
  • The Paxton kit requires a hole be made in the oil pan. Does anyone have experience doing this? Curious to hear how you did it? Did it with the oil pan still on the car? Remove the oil pan and drill it?
I'll pay to have the car dynoed and tuned by someone with more experience than me after I get everything installed.

This engine is not the end goal for the car. I want to build a 360 set up to take on boost in the future (650 hp) but this is maybe 5 years down the line. I am hoping that the supercharger and holley EFI system will be transferable to that new engine. For now I just want the car to be more fun and not worry about breaking down. Not going to be a drag car. Just want to feel some punch driving it around :)
That compression is a bit high for boost. That said, the Bullet Mustang from a few years ago had I believe 11:1 CR and could be supercharged. Electronic engine control and careful tuning is the key. Holley Sniper would be good for fuel management. Now spark control is a ticklish point here. Setting up a conventional distributor would be difficult. I believe the company is Precision Distributors. They sell a programable distributor that you program using Blutooth from your phone. It has a MAP sensor in it to function as vaccum advance and also works on boosted engines for boost retard.
The low boost you describe should not give trouble with conservative tuning. When cruising and the intake manifold is under vaccum you can have more advance, but as soon as you get into the throttle and the manifold starts seeing positive pressure the advance needs to be dialed back and probably the mixture richened up a bit.