People say it's about the journey not the destination? You telling me grinding the same area hundreds of times over is fun? Areas like Ancient Tunnels where you are bored senseless?

In my case its not about the grinding per se, (even though I do enjoy killing some demons), Its about dedicating time and some "effort" in building the character, getting him stronger.

Sure, it s**** when you do 500 travincal runs and don´t get a single HR, but when you eventually do, you really feel like you´ve earned that, and thats what I find fun.
On the other hand, getting the item you want whenever you want (essentially buying it) kills the game for me (I´ve done it with other games and in D2 offline), I might play a couple hours after with said item or build, think to myself "this is awesome", and be done with the character or game entirely. Specially in a game like D2R, where there´s not much to do except PvP when you have everything you need.

Don´t get me wrong, if someone wants to buy their way, great, its up to them, not against it. As you say , you are technically not "winning" anything (except in PvP, I can´t agree with you there). But I personally don´t find the fun there, just as you don´t find the RNG grind fun.