Melbourne is one of the great cities in the world (NY Times ranked it the 3rd best to live in a few years ago) however it requires local knowledge as most of it's charms are not visible to tourists. You live in Redwood City, and I would say Melbourne is significantly better than San Francisco (which I know well as I lived in SF for many years). Brisbane has changed a lot in the past decade (so has Melbourne, but over 20 years instead of 10), and half of the people in Brisbane seem to be from Melbourne (moved for the climate). Brisbane is a great place but provincial town is a good starting point for description. You can spend 10 years in MEL or SYD and keep finding new things; that won't be the case in BNE. San Jose is a good analogy to Brisbane if we are sticking to Bay Area metaphors.

Now if you want sleepy but nice, try Adelaide. Great place, but really a step back in time, even today, and quite a contrast to SYD and MEL.

Finally, I've found nightlife in Melbourne to be astonishingly good. 10x better than in San Francisco, for example (and that is about the best there is in the US). Sydney is often famous for its nightlife (more so than Melbourne), but I suspect that is just better marketing and tourist orientation. The gay scene is bigger/better in Sydney, but otherwise Melbourne has better clubs and nicer people as well as 10x better live theatre than Sydney (quite surprising). Most of the major shows open in MEL first and move to SYD after a year (e.g. Wicked just did that). MEL is the