Yeah, it's tight. You can do it on a min corruption playthrough, but you'll wind up with near nothing afterward. $1000 for winning Alice's poker game back during the Mafia arc, another $1000 for hunting the Gorgon successfully, $2000 for fighting the Asura with Nico, and then $49000 for dropping out of the tournament and not getting caught. $53000 is enough to get you both the Skill bones, Vortex Stone, Raffle Ticket, and then you'll be completely wiped out. Or go for the Power bones instead and have $3000 left over. The soda isn't necessary, if you didn't get caught infiltrating Langdon's office and picked Power for what you want from Tiffany, you'll have enough to pass the check it helps you with.
I wonder what the purchases the MC might have to make later on will be, though. Shopkeep offering to trade Power for money suggests that there will be things he needs to buy, but I don't know what. All the really useful stuff comes from Shopkeep anyway, everything else you can spend money on is things like a few relationship points in Amber or Emily's routes. Maybe we'll have to bribe someone or something like that, I don't know. But if money is to be valuable again, taking Shopkeep's conversion offer might be worth it over going for Skill gain or Corruption reduction. I dropped a save at the shop just in case.
EDIT: Actually, come to think about it, the Vortex Stone really isn't that useful if you didn't buy the Spine as well, so if you're going for the Power bones instead of Skill bones you can skip it, giving you an extra $15000. That's not a bad amount to have going into the next update, $18000.
