I finally got around to looking at Private Wakefield's papers from the National Archives at Kew. Some more information has come to light:
(1) He was born in 1897 in Kingstown, St. Vincent and may have a very tenuous connection with St. Kitts, Nevis and Anguilla.
(2) By 1914 he was attending St. Paul's School in Hammersmith Road, London (the school is now located in Barnes).
(3) He was called up while attending the school as a 'Medical Student' and joined the East Surrey Regiment as a private.
(4) On the same day he was attached to the Royal Field Artillery Officer Cadet training school at St. John's Wood, London. This was because he was a member of the Officer Training Corps (OTC) at St. Paul's School.
(5) He died about a month after enlisting due to disease.
(6) There was some disagreement between his father and the War Office regarding what should be written on his remembrance scroll and plaque. The official line was that as Officer Cadet was not a rank the inscriptions would read 'Private Ivor Mccrae Wakefield - East Surrey Regiment'. His father thought otherwise and that he should be noted as an Officer Cadet not a Private. After some discussion internally the War Office official line was that 'attached to RFA Officer Cadet school' could be added to the Scroll and Plaque.
His father/family must have felt very strongly about this as he is remembered as an Officer Cadet not as a Private on the family grave (not a CWGC maintained grave) in Richmond (London) cemetery.
His father, Arthur Wakefield, was a Bank Manager probably with the Colonial Bank (later part of Barclays Bank). He must have spent some time in St. Vincent as his two daughters were born there as well.
Some more questions are raised but it may be difficult to answer them easily such as his connection with St. Kitts. Something may turn up though.
