NGP mechanism vs the simple carbocation mechanism Question:

Predict the product of: ($\ce{C^*}$ is a $\ce{C^14}$ carbon)


My attempt:
I simply assumed the super-leaving group $\ce{-OTs^-}$ would leave, forming a primary ethylbenzene carbocation. That would rearrange via a hydride shift to form a secondary carbocation on $\ce{C^*}$ atom. The nucleophilic $\ce{-OH}$ group of the $\ce{-COOH}$ group will then attack and lose a proton to form 1-phenylethylethanoate (with the ester linkage at the $\ce{C^*}$ carbon):

However, my book has instead taken a different route. In the very first step, after $\ce{OTs-}$ leaves, they have taken the NGP mechanism and formed this transition state:

and said that now the $\ce{OAc-}$ will attack either of the two carbons (in that trigonal ring). Hence, according to their logic, both types of 1-phenylethylethanoate will be formed - one with the ester linkage at the $\ce{C^*}$ carbon, and the other at the $\ce{C}$ carbon.
My question:
I have confirmed from Clayden (Chapter 37 Rearrangements page 976) that the product ratio is indeed 50:50. So:

Why is the NGP mechanism being favored here over the other mechanism I described, even though the NGP mechanism involves a loss of aromaticity?
Are there other cases where the NGP mechanism dominates over the simple carbocation mechanisms, or is this the only such case?


Source: MS Chouhan; Advanced Problems In Organic Chemistry; 11th ed; Q16 in  Alkyl Halides (Substitution)
From Clayden (Chapter 37 Rearrangements page 976):


  Intramolecular reactions (including participation of a neighbouring group) that give three-, 
  five-, or six-membered rings are usually faster than intermolecular reactions.    


It also gives the exact same example as your question:


  


Notice that both products are given to be exactly 50% each. 

NGP is very often faster than bimolecular reactions as for the latter to take place two molecules have to collide first.   

1:1 ratio can be attributed to the fact that in NGP the transition state involves loss of aromaticity BUT NGP supports the ionization of the starting material. 

There are a lot of examples  this one reaction isn't a black swan. Interested readers may see chapter 36: Participation, rearrangement and fragmentation in Clayden to find more details and examples.