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When a person has surrender his citizenship as a Malaysian and obtained PR/citizenship in another country, then he decided to purchase a property in the original country (Malaysia). Is he subject to the foreigners criteria? Any loop hole?  

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buy property under family members name will be one options.

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if you are Singaporen you also can buy property property in Malaysia.

but only you can't not have property in Singapore (HDA) = Flat apartment is government house, if you buy condo is no problem. so better you check the person where is there country. have any Art in there own country.

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What if the person actually holds dual nationality? Does he still subject to the foreigners criteria? 

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PR/citizenship also same.

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giving up Malaysian citizen & getting another one in essence the person is a citizen of that new country.... so RM1mil residential prop rule applies..

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Way back in year 2008... I believe people who own Singapore HDB can still purchase property in Malaysia without restrictions... Now HDB have since changed the rule.

Yes if you buy Condo or private property in Singapore, no restrictions.