The ninth chapter of Final Fantasy 7 Remake is one of the biggest highlights of the game, and part of it is because of all the fun side-quests you get to do. It's a lot of fun, but there's a little more to this particular chapter's side-quests than others. Below you can find a detailed walkthrough of each Chapter 9 side-quest and the rewards you get for completing them.
To get the Chocobo Sam quests ("The Party Never Stops" and "Dynamite Bodies"), agree with Johnny at the Honeybee Inn, choose heads or tails at the coin toss, and choose the "poor man's" option for 100 gil at Madam M's.
To get Madam M's side-quests ("Price of Thievery" and the "Shears' Counterattack") disagree with Johnny at the Honey Bee Inn (or don't follow him there), choose not to play at the coin toss, and choose the "luxury" option for 3,000 gil at Madam M's.
If you mix and match your responses, the side-quests you receive will be based on whichever set of answers you favored most. So disagreeing with Johnny, for example, but calling the coin toss and choosing the poor man's massage will still get you Chocobo Sam's quests.
Other items may also factor into which set of quests you get, but based on our experiences, it's still hard to say how much. Talking with Johnny's dad in the inn and outside Corneo's Colosseum seem to count toward Chocobo Sam's quests. How you describe Tifa also may influence the decision; saying Tifa is in great shape seems to count for Chocobo Sam, while saying Tifa is a great bookkeeper seems to count for Madam M, with the "great fighter" option being neutral. In general, it seems that if you want to access the Madam M set of quests, you should side against Chocobo Sam and generally pick options respectful of women.
On your first playthrough, you can only experience one of the two sets. If you're eager to experience the other pair, you'll need to replay Chapter 9 using the Chapter Select menu that becomes available once you finish the game. Regardless, both sets are required to complete the "Best in the Business" Trophy. We've detailed the different quests below.
Agree with Johnny at the Honeybee Inn, choose heads or tails at the coin toss, and choose the "poor man's" option for 100 gil at Madam M's.
The Materia Shop owner will send you to the Inn to use a vending machine, where your Assess materia will be tested. After that, drop by the restaurant and help the owner with whatever your best elemental materia is. Finally, the Item Shop owner will send you to deliver medicine; depending on the level of your Cleanse materia, you'll deliver more medicine for more rewards. Check the bathroom at Drunkard's for your first delivery to get a sedative. The second goes to the alley behind the gym, accessible from the northwest side of the map, and gives you a celeris. The third is for the narrow alley just north and east of the Item Shop, which will earn you a pack of three Big Bombers. After you're done with the medicine, the Item Shop owner will give you the "Inspiration" to bring back to the dressmaker and complete the quest for a Turbo Ether.
Avoid hitting the Bombs when they do the Inflame move, because that'll cause them to grow in size, making their attacks more potent and expanding their range. Do your best to keep away from the Bombs and keep pushing their stagger meters up until you can close the gap and take one out with Punisher attacks and ATB abilities. At that point, finishing off the other should be pretty simple. You'll get an Arcane Scepter weapon for Aerith for your trouble.
Disagree with Johnny at the Honey Bee Inn (or don't follow him there), choose not to play at the coin toss, and choose the "luxury" option for 3,000 gil at Madam M's.