Admittedly, I have already sold a few watches to (partially) finance OTHER watches.
In two cases I sold a watch because it no longer felt 100% correctly and bought an improved model years later, which I am still very happy with.
Selling s Rolex Day Date 36 mm in white gold with silver dial and smooth bezel. 
Years later: Buying a Rolex Date 40 mm in white gold with fluted bezel and olive green dial. 
Selling an IWC Da Vinci Perpetual Calendar 1st gen. in white gold with 39 mm and white dial. 
Years later buying a Da Vinci Perpetual Calendar Rattrapante 2nd gen. in platinum with dark blue dial. 
All the best
Thomas
P.S.: Your Santos looks great on your wrist!