linesforeyes --
Welcome to FlyerTalk!
The questions you ask are excellent ones. The biggest problem that I'd foresee is finding a balance between your budget and the bespoke clothing that you're looking for. You could certainly get excellent fabrics -- ones that both look great and that stand up to regular use -- and wonderfully-fitting clothing from the upper-end tailors in HK, but not for the price range that you list. If possible, you might consider buying fewer clothes but higher quality -- but ultimately it's your decision how to make the trade-offs.
All that said, an especially knowledgeable source of information about bespoke clothes is the
Ask Andy Forum. If you haven't visited there yet, I'd strongly recommend it.