That pin can be found for $30 or $35 on on ebay here and here, where it is described as being from the 80s and as an "employee pin".

I was thinking that this might have been something aimed specifically at technology buyers in US schools in the 80s or 90s, to whom Apple offered substantial institutional discounts in a (relatively successful) effort to dominate that sector. However searching the phrase "does more costs less" i found this TV spot advertising the Quadra 605 which at $1000 was the cheapest computer Apple sold when it was introduced in October 1993 (and allegedly cheaper than something else they refer to as "PC Leading Brand" 😂). That system was sold under the LC and Performa brands up to 1996, but it was only sold as a Quadra until October 1994, so, to answer OP's question: that slogan was in use at least sometime in that year.