1 & 2... Depends on which company he's from, and what is his experience. Generally, the companies in Singapore don't think highly of their counterparts in other countries. Malaysia included, although not as bad as our Asean neighbours or India or China. But they certainly don't think our companies have equal standards, service quality and professional ethics as Singaporean, Hong Kong, Japanese or ANZ companies... especially the ethics.
However, within the industry and within companies at par (eg. coming from the KL office of a global MNC to the Sg office of the same or similar global MNC), the equivalency of your value is much more appreciated.
3. The biggest challenge, in my opinion and from an ethnic Chinese perspective, is the realisation that those attributes that made you stand out in Malaysia and handed you an auto-win over 70% of the Malaysian population (ie. the hunger or motivation to work hard because you know you will starve if you don't, being trilingual and for many, having a foreign degree) is effectively neutralised in Singapore. Everybody speaks English (in most cases better than you, 75% speak Mandarin (in most cases better than you) and the entire population of this generation has at least a poly diploma or better. On top of that, Singapore is home to hundreds of thousands of highly qualified first and second generation immigrants that are all too willing to take your job away from you.
The competition, therefore, is stiff!
Thanks..Look like a challenging path for my friend who currently worked in local listed company (not MNC).