That is all really interesting and does a good bit to flesh out the story, although it still remains fairly dry. I've looked through all the sources I have here and checked my notes again and I will paste the results below. I think that Elers misremembered the name of AW's ship (which was the Princess Royal, not the Princess Charlotte - if Hobart got it right). I do hope you find the account of AW playing cricket at Cape Town - that would be fun. And that you publish the results of your research when you've completed it.

Here are my further notes:

The Voyage to India, 1796-97

Capt Dowal wrote to Sherbrooke from Cape Town, 6 August 1796 applying for leave to return to Europe on the basis of ill health, and promising to either rejoin the regiment within six months or transfer to another. WP 1/3 [I don’t think leave was granted – see WSD vol 1 p 136-7)

Hobart to AW Fort St George 11 January 1797 thanking him for his letters from the Cape and from on board the Princess Royal, and agreeing with his decision to proceed with the regiment direct to Bengal rather than calling in here en route. (WP 1/3)

George Elers (Memoirs p 58) says that AW proceeded from the Cape to Bengal on the Princess Charlotte Indiaman – I follow this in my online commentary to volume one, but Hobart’s letter suggests that Elers misremembered the name of the ship.

AW to General Cunninghame Fort William 9 March 1797

‘We arrived here about three weeks ago after a most tedious passage from the Cape of Good Hope…’

Webb’s History of the 12th Regiment p 186 states that the convoy reached the Cape on 19 September and sailed on 10 November. Pulteney Malcolm however seems to have been at the Cape as early as 4 September, which may mean that he had sailed ahead, or that Webb’s date is incorrect. Both Webb and Elers state that the men of the 12th did not disembark which seems remarkable but is presumably correct (although Webb may be relying on Elers for the point).

The Memoir of Sir John Coape Sherbrooke that is appended to Life and Letters of the Right Honourable Robert Lowe, Viscount Sherbrooke by A. Patchett Martin (London, Longmans, 1893) vol 2 says: ‘On April 6, 1796, Colonel Sherbrooke sailed with his regiment to India, disembarking at Calcutta, February 16, 1797.’ No source nor any further detail.