I paid $1,500 for a new Omega Speedmaster Pro in 2000.... It's now worth ~$4k used.
I paid $800 for a vintage Speedmaster Pro in 2003... Its now worth ~$9k.
Back when I was actively collecting i never lost money on a 'quality' watch.
Even my everyday beater watch (Marathon SAR) was $200 when I bought it.. and now worth about $1,300.