YES!!! Something to do with fluctuating your bets must have some effect. I tried to do Gambler #8 for around 2 hours... Only had 1 out of 3 needed... I started increasing my bids (20 cents the first time, 30 cents the next) and won each hand with 5 cards total. I completed the next 2 for Gambler #8 within mere minutes.
It almost felt like an exploit! Wow!!
Thank you for your post, @Jess1322!