When I was younger and had less money I bought used, from a dealer. As I got older and my purchases were much better thought out and expensive I would keep a component for ten to twenty years. For instance I bought a new Pass x350 and traded it in 15 years later for $500 less than I paid for it… final cost $2.77 / month. What a deal.
So, first. Having a dealer that accepts trade-ins is important. This gives him the opportunity to give you a “discount” from MSRP under the guise of “trade-in”… that does not violate their agreement with the manufacturer. My dealer got out of the business of reselling… he gives it to a third party that resells on the internet.
Having a long termed relationship with a dealer is useful as well.