In 2005 I set a goal to read all of Waugh's novels and travel writing that year. It was time well spent. My favorite turned out to be the Sword of Honour trilogy, but I've re-read Put Out More Flags the most, and probably thought about Helena the most. Understanding Waugh's perspective makes it easier to laugh at all the silly social movements, businesspeople and inept bureaucrats that plague us without succumbing to cynicism.
His diaries have interesting bits, but as Paul Fussell remarked, Waugh wrote the diaries at night after drinking, and the letters in the morning sober. I have a volume of his and Nancy Mitford's letters to each other; I must say that her prose would look better on its own.
I don't think that it was that odd a name for a man back then. And fashions change. The critic Clive James started life as Vivian Clive James, at a time when the most prominent Vivian in Australia was a (male) cricket player. Then they filmed "Gone with the Wind".