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1916, he was responsible for road works in New Kowloon and the New Territories, extending the network of metalled roads in the Territory. By this time he was on a salary of £630 per year with a conveyance of £360 per year (presumably to cover the costs of running a car).
Jackman married Dorothy Smith in the Peak Chapel on 26 August 1910. Dorothy Smith had come to Hong Kong around the beginning of the century with her brother, Crowther Smith, who had a legal practice in Queen's Road Central together with F. X. d'Almada e Castro. Also in Hong Kong at the time was Dorothy Smith's uncle, Horace Percy Smith, a well-known accountant and eminent Freemason. Immediately after the wedding, the couple went off for their honeymoon in Macao with a very rowdy send-off at the Macao Ferry Pier. So many firecrackers with red confetti were set off at the pier that one paper reported that the couple were mistaken by passers-by for the Governor of Macao, and many people joined the crowd to see what was going on. After their honeymoon, Jackman and his wife lived in Des Voeux Villas on the Peak. They had no children.
H. T. Jackman was the father of urban planning in Kowloon and New Kowloon. In the early part of the century, development in the territory of Hong Kong had mainly been restricted to the island, while Kowloon had provided bases for the Army as well as major wharfage areas. The construction of the Kowloon Canton Railway greatly increased the development value of Kowloon and the population there started to grow rapidly. The land necessary for the Railway station, shunting yards and workshops was reclaimed from the sea to the east of the Tsim Sha Tsui peninsula (the hongs having taken up much of the available land to build godowns in anticipation of the opening of the railway). Writing in 1908, H. A. Cartwright, felt that “it requires no great prophetic instinct to predict that in time, the whole of Hung Hom Bay will be reclaimed.”
From 1919, Jackman was closely involved in Kowloon town planning. Many of the old villages in the area succumbed to development clearance: Kau Lung Tsai and Kowloon Tong villages gave way to town house developments which are still there today.