...I'm still item farming with Wil and Irwin, but with Jack...
...He's currently an S3 Sp. Jonin (Gen) Legacy with Inner Wastelands unlocked, six bloodlines (haha Eye of the Storm and Power of Greass are awesome for being looping bloodlines), and is currently farming Ninja-Mas items to pass the time.
Also, it IS possible to easily pass the 15d/4s check... If you fully enhance Attack on the Nervous System and hang out with The Rack. That SHOULD bring the chakra cost of it down to 375. There's also other free jutsu such as Nadeshiko's Goth Goth (that is EXPENSIVE on your stamina), the previously mentioned Welcome To Good Burger (that's what I used with Irwin to unlock Outskirts in S2), fully-enhanced Dance of the Crescent Moon (with a Sicko hangout), and since you're a WhiteEye, you also have Eight Trigrams Eleventy Billion Palms as an option (and it's decently cheap to enhance, too! 75K to learn since you're not a Jonin, and another 500K to fully enhance so it'll only cost 500 Chakra? Yes!). Redeye have the option of abusing Emosuke once they get up to Sp. Jonin for Emo2's Right in the Eye or (provided they're given the extra Billy Buckets) Emo3's Get In The Bucket. Legacy have more chakra they can do stuff with, so all they need is a Rack hangout and that's instant win right there.
A LOT of this is assuming you have at least the Letter of Marque. If you have that AND Plug Suit, well... Passing Revenge becomes cake (two automatic Gen successes and the Sword Call, to be specific).
I'll say this: scheduling hangouts is your best friend.
Silly me EDIT: ANY bloodline can do The Rack hangout -> Attack on the Nervous System. All it takes for WhiteEyes and RedEyes is using the Chicken Ramen while they're fully charged.
Extra edit: Heck, if you need it, I'll even send you a Make-Out Mood Enhancer. Just tell me if you want/need it.