FWIW, milking really isn't that big of a chore. It can be as big of a pain as you make it to be. I had no problems milking my goats 1x day (usually around the same time of day) last year and plan to do the same this year. I milk in the evenings after I get home from work as that's what my...
I might have missed it, but I don't think anyone has mentioned Nigerian Dwarfs as a breed to consider. There are some great milking lines out there, they are smaller in nature and just as friendly as they come.
You said you'd rather not separate males from femals - the only way to do that is...