He was a member of the Brixton Chess Club
Bushey Lodge was one of the largest in the neighbourhood - the Jacobs family would have needed the space, what with Herbert, his three brothers and his four sisters, the staff of four, not forgetting two parents: Edward, a "merchant", still only 43, and Alice just 38 (who had borne eight children by the age of 32). Incidentally, John Brown, the encyclopedic historian of Streatham, explains that a previous owner, earlier in the century, was William Evill aka Mr. Schweppes (after he bought them out in 1834). Evill moved to Streatham to facilitate his promotion of you know what at the Great Exhibition of 1851, where they sold over a million bottles. He bubbled away in Bushey Lodge until 1877.
Herbert, and (I'm assuming) his chess-playing junior brother Harold, went to the prestigious Whitgift School in Croydon - there was an omnibus door to door seven miles south. After Whitgift, he studied for, and acquired in July 1883, a BA in German at London University (per documentation in the Inner Temple Archive, with thanks), so presumably he had finished his schooling a few years earlier. In 1883 when he was admitted to the Inner Temple, when the family address was given as 17 Morland Road, Croydon. He was called to the Bar in January 1887 when his father's address was given as West Lodge on Denmark Hill.
(Source Streatham and Brixton Chess Club)