Evening Andrew;
For a sensible, reliable, useable but 'tweaked' 500, I wouldn't go above 695/700cc. Too much above that capacity and you run the risk of the engine running hot. Being that you are in Sicily, I would suggest that you look at finding a complete Mk2 '126' 652cc engine, and tune that engine whilst you continue to run the engine in the car at the moment.
Going the '540cc' route is the easiest way to give yourself a bit more grunt, not a lot I will concede, but definately more. Just increasing the bore size will raise the compression ratio; whilst the head is off for the conversion, have it skimmed slightly (but it is important that you leave the 'exhaust-blow' ring on the head intact). Abarth never went above 10.5:1 compression on his 595/695 models---I would suggest that you go no higher. As well as fitting the slightly larger pistons/barrels, fit a 28IMB carb--comes off a Mk2 (652cc) 126.
If you want a list of the people that can supply 695/700cc conversion kits, contact me direct and i will give a list of suppliers of such kits.
Also, when you take the car back to the USA, it will be a 'foreign' car, with not a lot of back-up there---reliability will be more important that outright performance.