Quantity vs. quality is always a question, although both are relative terms. But I see two situations in which this comes into play for me: One, do I buy one $300 watch or two $150 watches? That's the most common "dilemma." The other that I've thought about, which hasn't actually happened yet, is whether to buy 8-12 ~$200 watches over the course of a year or save up my dineros and splurge on a semi-luxury watch like a Chase-Durer, more expensive Seiko, or even a Tag Heuer. A Tag Heuer Aquamancer costs about $1500+ - and I've spent well over that in the past year on cheaper watches. My personal ethos tends towards "quality over quantity" but I'm finding myself not wanting to apply this to watches. Part of the fun of watch collecting is getting a new watch. If I bought one new watch a year, I wouldn't have the joy of opening that box once or twice a month. On the other hand, buying too many watches - like I did this summer - leads to a feeling of trying to fill the never-ending void and buying into a consumerist mentality like we teach our children who look for the next present before fully unwrapping the current one. So after a first year+ of being a "serious" watch collector, I'm finding a balance.
I'm currently culling my collection down to less than twenty watches, paying off most of the debt that I accrued earlier in the year, and trying to find a more moderate, balanced approach. I don't see myself spending more than about $300-350 on a watch in the foreseeable future, and I've toned down my spending so that over the last couple months I've "only" spent a few hundred dollars (things really got out of hand in June-August). In the future I can see myself getting a semi-luxury watch ($500-1,000), maybe even a low-end luxury watch ($1-2,000) like an Invicta Valjoux or Tag Heuer, but it will be years if ever that I purchase a true luxury watch ($2,000+) like a Breitling Super Avenger (~$4-5,000).
Until I get to the point that I've run out of moderately priced watches to buy ($1-300), and then expensive non-luxury watches ($3-500), I see no reason to go into deeper waters. The simple truth is that I don't like semi-luxury watches that much more than watches costing half or a third the cost, and the higher the price the less of an increase in relative quality and desirability. To put it another way, I'd rather own a dozen Seiko Velaturas, Sporturas, Invicta Specialty Reserves, and Citizen Eco-Drives, then one low-end Breitling. It is simply more fun that way.