Clotho, Black Moons - I suspect that you're both right, just different ends of the same question... not that if it's possible to 'charge - but is it worth it?
The snag is diminishing returns, can you provide boost enough to overcome the loss in providing it? With the very simplistic HT engines, prolly not. Even if you managed a pressurized state - you'd loose so much, charge through the ports & power making it that you'd end up with a loss. TBH if I were to try 'charging any engine I'd start with a platform better suited even if a two stroke for their raw power to weight advantage - it'd just have to be of better construction if nothing else. I love the HTs don't get me wrong, but there's issues even with high compression mods (bearings, crank failures etc.), let alone a boost condition.
I started looking into small four strokes w/the thought of supercharging on my mind, turbos wern't to be ignored tho I prefer the benefits of supercharging. The more I looked into it, the more questions came up instead of the answers I was looking for - the one constant being ofc "diminishing returns", that the 50cc displacement range was woefully problematic, and very, very few folks had any success.
I'm not sayin' it's impossible ofc - but is it worth it? I've no idea - not being an inventor I decided to set that 'un aside for others to deal with and went another route