S + Had ever been to do? Pleasant lot?

Hi everybody,

I'm reading The Adventures of Sherlock Holmes and there is this sentence in The Noble Bachelor that I can't fully understand:

-- A gentleman entered, with a pleasant, cultured face, high-nosed and
pale, with something perhaps of petulance about the mouth, and with the steady, well-opened eye of a man whose pleasant lot it had ever been to command and to be obeyed. ---

I mean the part from 'whose' to 'be obeyed.'

According to the dictionaries I have consulted, 'lot' has a number of meaning but which one is the one C. Doyle specifically used here?

And then the 'had ever been to do' structure? This is the first time that I've ever seen it in writing.

I'd really appreciate it if someone can shed some light on the matter.

Many thanks.