Is financing also a factor to consider? If both names are included in the property, then both incomes can be used for the loan application.
Regardless of sole or joint ownership for 1st property, your stamp duties will be 3% approx, as you probably will qualify for ABSD remission if its your matrimonial home and jointly owned.
For the 2nd, perhaps its difficult to conclude since by the time of your purchase, ABSD rates would have likely revise. Thanks and is there anything I can assist further?
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Option would be good.
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If you understand the different rates of ABSD applicable in the scenarios you have provided above, perhaps what would make the difference will be the quantum price you are working on the individual properties and the sequence of purchase.
If you need some read up on the rates applicable, perhaps you can go to http://www.iras.gov.sg/irasHome/uploadedFiles/Other_Taxes_and_Services/Stamp_duty/xxx/ABSD_Rates_for_Joint_Purchases_Made_by_Married_Couples_and_ABSD_Refund_for_Purchase_of_Second_Residential_Property.pdf for reading up.
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