ContestID67 wrote:
I am thinking of moving up to a DG-300 or DG-303 (winglets!) and wonder
if it also holds its value as the DG-101 does?

300, yes, they have held their value pretty consistently over the past
decade or so. The 303 is a bit more complicated, as it is in the price
territory of perceived "better" standard class gliders like earlier
Discus and ASW-24 models. My 303 was definitely more capable glider
than my 101, but the increment in performance and fun factor wasn't
really worth twice the price to me. In terms of bang for the buck, the
101 beat it by a wide margin...

Marc