gentleman of the round
[play on SE gentleman of the round, ‘a gentleman soldier, but of low rank [...] whose office it was to visit and inspect the sentinels, watches, and advanced guard. It was, therefore, an office of some trust, though little dignity’ (Nares, Glossary, 1822) + pun on one who ‘does the rounds’]
[late 16C–early 17C] a discharged or invalided soldier who makes his living by begging.
gentleman of (the) three ins
(alsogentleman of the three inns)
[late 18C] ‘In debt, in gaol, and in danger of remaining there for life; or, in gaol, indicted and in danger of being hanged in chains’ (Grose, 1788).
gentleman of three outs
(alsogentleman of (the) four outs, gentleman with three outs) [vars. include ‘out of pocket, out of elbows, and out of credit’ (Bulwer-Lytton, Paul Clifford, 1830); ... of the four outs, ‘without wit, without money, without credit and without manners’ (Hotten, 1864)]
[late 18C–19C] ‘Without money, without wit, and without manners; some add another out, i.e. without credit’ (Grose, 1785).