I have been a serial flipper and buy in bundle deals to get the sports pieces. It's hard to get sports pieces from ADs here in Malaysia, never mind the premium. When I began the hobby many years back, I've heard the same o' "Rolex bubble will pop, wait till price drop to buy." but one could see the sports pieces' real world pricing climbing higher and higher. The only Rolex pieces that you could buy cheap (and I use the term loosely) are dress watches e.g. Day-Date and Datejust, and sports pieces e.g. Explorer and Milgauss, to an extent. Or pick them up from the secondary market and these examples would be even much more discounted, especially now that 2019 saw newer movements fitted for the DJ36.
Sports pieces are a different ballgame altogether. Once discontinued, the prices go mad. I remembered flipping many pieces of Batman last year (have to check my blog to be certain, but it was a couple of pieces every other month) and prices were circa RM40k+ each. Just the other day, a collector whom took 2 pieces (1 to wear and 1 to keep for his son), told me that a grey reseller offered a very high trade-in for the unused, unnamed and undated piece he took from me. He flipped it for an AP; and a subsequent listing came up at RM70k thereafter. I thought that was too high a sale price from the grey reseller, but it was sold in a flash!
So if you want to have your cake and eat it too, go for the Rolex sports pieces. You get to wear it; and then when you get bored of the piece some time down the road, sell it to cover your cost or even make some profit thereafter. Or better still, just put it into the safe and wait for it to appreciate higher.
There's always an alternative of course. Just go for other brands. Omega has the Seamaster 300 and Planet Ocean, and these go for great discounts in the market. If you don't limit yourself to a Rolex on your wrist, there are way more bargains out there in the market.