Choosing polar aprotic solvents for substitution reaction

1. It is known that common polar aprotic solvents include acetone and DMSO. Since they do not have hydrogen bonded to highly electronegative atom, they cannot only form dipole-dipole interaction with nucleophile, instead of hydrogen bond & ion-dipole interaction.

2. Moreover, the electrons in 2 R-CH3 groups in acetone / DMSO are repelled by electrons of the nucleophile, hence increasing the distance of dipole-dipole interactions, further decreasing the solvating effect.

My question is: from (2), is it better to use reagents that have more bulky R groups linking to the partial positive atom like pentan-3-one & diethylsulphoxide instead? I know this will decrease the polarity of solvent, but won’t these better decrease the dipole-dipole interaction hence further increasing the nucleophilicity?