I'm amused by the exploits, but I think the existence of Honor Mode invalidates the idea of 'for convenience' exploits, since we clearly have a hardcore mode that's meant to be hardcore and not just for personal bragging rights. And they're not quite funny enough for me to want to preserve them (a la skyrim's thievery via placing kettles on the witnesses's heads.)
But the amount of gold you have to spare is super dependent on your avatar character's charisma. My two most recent playthroughs were a bardlock and a rogue, and the rogue was barely scraping along until Act 3, having to let several items of interest go in Act 1, while the bardlock had money flowing out of his every orifice. The difference in the buy/sell rates is huge. I mean, I eventually started bringing Wyll along to all of my major transactions, but I suspect most players are like myself in that they either forget to minmax or, for a significant while, don't realize what and why they're missing out.