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Also when starting a run, you can restart a few times to make sure your 1st round is meaningful (good joker, or making good money or whatever)
To answer your question, I believe I cleared it all in one evening after unlocking hearts/spades deck.
Though this challenge is probably the most RNG-dependent the game ever gets, so estimates aren't going to help much. But no amount of RNG is going to help if you pass up the right things when you get them.
I got an early Delayed Gratification, which pretty much allowed me to sell Credit Card and start building up tons of cash. Was relying on just Swashbuckler at that point, so just filled up my joker slots pretty quick. Lucked into Dusk and Acrobat because I got to reroll a bit with all that money (also bought the cheaper rerolls voucher). Got a blue seal from a spectral pack and used it to get flush to level 10 by the end (got terrible planet pack rolls). Got the Holo Fibbonaci from a buffoon pack. I also would've died to Violet Vessel, but was lucky enough to see Mr. Bones in the first shop after the boss. Was a great reminder to always check what your upcoming boss is in Run Info after you beat the last one, saved my hide.
'Just use a deck"... during a challenge? If you don't know what Golden Needle is, why respond?
That person was probably thinking of the boss, "The Needle."
I just beat it today, I don't know how many tries it took because I don't keep trying when it doesn't work. I just come back to it from time to time. I think I made less than 20 attempts.
Through this part, I was able to quickly have a good saving with "Mail in rebate" (excellent for this challenge, we gain more from discarding than we ultimately lose money) and also and "golden joker", I quickly got rid of the credit card.
I played flush (level 6 only at the end of the game).
It was enough with "Acrobat" (X 3 because as a reminder we only have one hand, so it's the last one so X 3) I also had "The Duo" (X2; because I had converted a maximum of card in the same color, so many pairs), I also had the "Blueprint" and finally bought just before the final boss "Ancient Joker - which was initialized with the heart color, the color that, luckily, I had favored).
There must be quite a few ways to beat this challenge, but economy is key.
I was quickly over $40 when I sold the credit card, by the end of the game I had over $100.
Nice
I pull a hearts +3 card, all hearts are de-buffed.
I get to round 6. final hand is to start with 0 discards.
It's odd how the RNG lines up perfectly against whatever I'm holding.