For most of my hobbies, I try to do this with specific pieces of equipment, if it's in my reach. I'm always hunting for discounted or secondhand version of a high quality product, unless it's imperative that it's new. Then I try to replace the less important pieces with better products as I go, when I happen upon a great price. I work near the Leisure Pro store in NYC, so that seems like a good place to try some things on and find a good balance of price/quality for my purposes, and hopefully score a good price on some closeout equipment.
Most consumers are drawn (psychologically) to mid priced products because of a perceived better value (it's not the cheapest but not extravagant), so some mid-priced companies take advantage of this and skimp on quality. Knowing that, I'm fine with generic if the value is actually good, because I know I'm not paying for the brand.
I am not saying to always buy most expensive at all. I am after best quality and also for the best value for my money. But I also sold my TV, bike and some other stuff to save money to buy the best dive equipment at that time when I was a college student and had a very fixed income I wouldn't buy the highest quality bicycle or sneakers but I'll do all I can do to buy the best regulator, BC, etc. for my diving. My life, comfort, enjoyment and passion fulfillment depend on it