In my experience, the amp makes a much bigger impact than the preamp. I was using an Outlaw 975 as my DAC and pre and then switched to an Odyssey Candela and Schiit Bifrost Multibit DAC. There was a difference, but it wasn't huge. I then "upgraded" my Odyssey Candela to an Aesthetix Calypso Signature, which is 4.6x more expensive than the Candela. I would not say that the Calypso is that much better.
However, when I upgraded my amp to a Sanders Magtech from Odyssey Kismet in Stratos monos, the difference was quite pronounced. I'm running Magnepan 3.7's. YMMV