TOPIC:

[born 1988 Enlisted (we believe in Winnipeg, Manitoba, Canada)
I think he was 18 at the time of enlistment.
We do not know regiment or other details. We have a copy of the letter his father Thomas May sent from Stonewall Manitoba Canada to Militia Defence in Ottawa Canada requesting information of John Duncan May's
health. He had received a notice That John Duncan May was dangerously ill with Enterce fever as was concerned. John recovered and continued his service in the Boer war. He applied for a land grant and was accepted.
John remained on his land in Transvaal, South Africa and died there in 1965.
We also have a copy of a news clipping he sent to a newspaper there which indicates they new him well, and state they " received a letter this week from our furthest subscriber J.D. May.
It says his address is:
J. D. May
P/B Matsulan Halt
P/O Box Warmbaths
Transvaal, South Africa

I have been completely dismayed that I cannot find a war record, or any other information on him.

I check with Canadian files and draw a blank, then British record and draw a blank I am trying to navigate South Africa and am drowning.

Can anybody help?

The South African National Archives has an on-line search facility for files kept in its various repositories. Given May's address, you could start with the Transvaal Repository in order to limit the number of options on the nation-wide one. There usually is at least a Death Notice, which can sometimes contain useful information.

Regards
Brett

My money would be on 1834 Trooper J D May A Division South African Constabulary as a candidate!