Ill let you know when I start it but I did wimp out and refit the valve lifter this time, I served a apprenticeship with british thumpers in my youth in preparation and I weigh a good 120kgs, removed the valve lifter on my sp400, just nudge it up to compression and lunge

Yes, its a kit I believe wiseco do the 94mm pistons now, but this one came from VD Classics (a thumper specialist shop in france) complete with matching liner etc via the magic of ebay.
A 15 isnt so bad for a xt is it? The supercharger on that bike is the same one I am using on my gs (SC12 doh, not a 11), it gives a displacement of 1200cc per rev, so I imagine its a fair bit underdriven rather than stuffing 2.4L into one 500cc pot (my engine is 860cc at the moment and Im driving at 1:1.5 engine/charger), and possibly he's lost some efficiency as a result. Plus theyre well known for causing intake charge heating above 12psi, so if he's asking for a lot of boost, he's probally being limited by detonation caused by that...
Have you seen the little clutches the SC12 comes with? theyre electromagnetically actuated, the same as on a aircon unit. If your worried about starting, maybe you could bypass the supercharger and flick a switch to turn the blower on madmax style (although madmax was faked, they used a electric motor to spin the gilmer for the effect). The toyota mr2 ecu turns the charger off during steady cruising to save fuel...
What you going to do about a cam? You want a soft cam with very little overlap in a blown motor or the supercharger just blows the charge through the motor during overlap, I imagine most aftermarket cam grinds for the XT would be anything but...