The use of the expression ‘polarity’ is not super accurate and very cosmetic because cosmetic isn’t an exact science and often performed by people without or minimal education in natural science; it would be useless for most manufacturers if raw ingredient companies indicated Hansen solubility parameters and the like… pretty much the same reason why HLB is still in use and not HLD-NAC.
From a chemical point of view, triglycerides are esters (one glycerol and three fatty acids) as much as ester oils (aka liquid wax, one fatty acid with one fatty alcohol). Hydrocarbons don’t have heteroatoms and are therefore more lipophilic (and have no polarity) whilst silicone oils (standard dimethicone, not modified ones) are even more lipophilic with equally absent polarity. ‘True’ polarity comes with alcohols (such as your mentioned Guerbet alcohol) and amines and other electron donating and withrawing heteroatoms. True, esters and amides impart that too but the effect is marginal, non-miscibility comes rather from other solubility parameters than ‘polarity’. There’s also a difference between miscibility and solubility. As a rule of thumbs, equal mixes with equal. ‘Polarity’ in the way you refer to it does rather affect emulsion type (lyotropic liquid crystalline phases) or, in common cosmetic language, HLB requirement (or apparent HLB values).