Hi Carol
His record as a Regular says he was transferred to the Army Reserve in January 1906. He would not have been discharged until he had completed his 12 years enlistment - ie in January 1911. You should read the printed parts at the top of the first page. As a Reservist he would have attended a two week summer training each year in exchange for half-pay; and been liable to be recalled if war broke out. In 1911 he would have had the chance of extending his service as a Reservist for a further four years. Which he clearly decided against.
Men often joined the Militia first as if they changed their minds about being in the army, it only cost £2 to purchase a discharge, compared to £20 as a Regular.
It is very difficult to tell Militiamen and Regulars apart in photographs, as the main difference was that their buttons and hat/helmet had a white metal badge rather than being made from brass. However as a Militiaman you would normally expect his shoulder badge to include an 'M' above his regiment (Essex). Here there is no evidence of a second row. If you have the original try looking at his shoulder with a magnifying glass to be sure.
So I think he is likely to be a Regular, and you can safely date the photograph to between January 1899 and August 1900 when he sailed to South Africa. In South Africa he would have worn khaki and on his return the cuffs had changed to a V design. Also he would have received his QSA medal by then. As he looks younger in the first photograph I think this was taken when he joined the Militia.
His record says he served with the Mounted Infantry in South Africa. The 'battle' phase of the war had ended by the time he arrived. During the guerrilla phase the normal infantry manned lines of blockhouses a few hundred yards apart and the Mounted Infantry drove the Boers onto these lines, burning farms as they went.
If you cannot find him using his name on the medal roll on Ancestry, you should try searching for just his number. He is on the second page. This confirms the CC, OFS. T clasps for his QSA. He received the Kings medal for serving at least 18 months in SA.
Ken
Added.. For completeness I suggest you contact their regimental museum and ask when they stopped using leather gaiters. If it was before 1899 then it cannot be the man you think it is.