The Era Magazine of August 1862 states that his song The girl in her dress of blue "will become popular".

Do we know what were the "difficulties that appeared almost insurmountable"?

I found the folowing in The Aberdeen Journal of March 22nd 1865:

"Harry Clifton, the inimitable comic singer, takes a benefit in the Music Hall on Tuesday evening next, when he will be supported by a talent of every variety. Harry deserves a full house, especially if the published statement be true that he had his savings in the Birmingham bank which has failed."