Hi there Ed,
In regard to your boss, he can pretty much afford quiet a spacious apartment in Happy Valley, which would be quieter than midlevels especially on the weekends. Pok Fu Lam is another location he could consider which offers superior sea views and mostly professional expat families.
As to your requirments, maybe consider locations that tend use buses as their primary form of late night public transport. Area's like Sai Kung, Hebe Haven, Clearwater Bay, even the Gold Coast Area of Tuen Mun ie (Siu Lam / Sham Tseng) could be a consideration, because at the hour you plan to leave work, the commute home is only 30 minutes. $8000 per month will get you a spacious pleasant view 3 bedroom apartment out here.
A photo of our view in Siu Lam below to give you an idea of what I mean.
Commute time in the morning however would be about 50 minutes for Gold Coast, and about 1 hour 15 minutes from Sai Kung.
It will all depend on what sort of lifestyle you want to spend when you are not working, if its going to be work and live in the city, or work in the city, and live in an affordable green bayside area.
If you enjoy sailing in your spare time, then Hebe Haven, Discovery Bay ( use the ferry to get home ), Sai Kung and the Gold Coast region will be best bang for your buck.