The thing is, Kyprianos can go IFR and that makes a flight like this a piece of cake compared to going VFR.
Especially when it comes to stuff like there being no current VFR charts for the Albania/Greece region, and Montenegro being a bit difficult over VFR routings through their airspace. Whereas if you go IFR, nobody cares so long as you managed to stuff a valid route into the Eurocontrol computer.
Personally I don't think the Alps are an issue. They have loads of valleys and there are also many "flat enough" bits where one could force land. I would hesitate in the case of a solid overcast but in SCT or better it's just fine. Obviously oxygen is a must but then oxygen is a must for any serious touring otherwise you are chucking away (on a TB20) the top third, and the most enjoyable and safest third, of your vertical operating range.
Kyp - drop by at my house and I will fill up your o2 kit for you
The most dangerous part on this trip will be joining the circuit at Stapleford, if arriving on a Sunday afternoon.