I saw the following reaction on Modern methods of Organic Synthesis by Carruthers. The reaction is about the selective alkylation of trimethylsilyl enolates, and is shown below.
[![enter image description here][1]][1]

However, I have some doubts regarding the formation of the enolate in the first step. 

 1. Why does deprotonation occur from the alpha carbon on the left, and not from the gamma carbon? Is it due to steric repulsion between lone pair of oxygen and negative charge on Nitrogen? But there two gamma carbons, and only one would be hindered?

 [![enter image description here][2]][2]

 2. The condition shown is the kinetic condition (LDA,THF, -78 °C). So the given enolate is the kinetic enolate. Is it classified as a kinetic enolate due to the lesser number of resonance structures (less stable alkene)?                  
     (Normally, if the enolate is less substituted, it is termed as kinetic, and more substituted one is the thermodynamic enolate)
[![enter image description here][3]][3]

 3. Should the carbanion stability of each resonance hybrid be accounted to determine the type of enolate?

Kindly provide answers to all questions precisely. Otherwise, please do not attempt. I really need clear answers. Thanks in advance.

  [1]: https://i.sstatic.net/iIKhu.png
  [2]: https://i.sstatic.net/OSuY0.png
  [3]: https://i.sstatic.net/3d91s.png