A Street Cat's Tale: All in One Run (Level 6 with all NPCs)
Because there are no trophies/achievements tied to endings and just the level 6 intimacy, it is possible to get all the trophies minus the house building ones in one run. I recommend fully upgrading your home before trying this.
If you get a good milk run going, you can work your way around the map and talk to all the NPCs in a day, and if you know what good gifts are for them, you can pick it up along the way (example: some flowers are in a pretty good spot to talk to Elder Cat and then pick up along the way to Sarah).
Some of the quests will require RNG like band-aids, big fish and the likes, but anything you know you may need for a morning NPC, you can try to grab in the spare time you have before going to bed as it carries over the next day.
This is just to show that you could do all 8 in one run, but you may as well get some while doing the house upgrades and I recommend Sarah as she is pretty far away. Please keep in mind that if you don't plan on doing them all in one go, still do the rounds in the first couple days to ensure everyone is at level two because there will be quests that require this.
Below I have written everyone's gift preferences and what each intimacy will trigger as a quest requirement:
Elder Cat (Likes Big Fish and Canned Food)
2. Leftover Fish
3. Reach Level 2 with boss cat
4. Big Fish
5. Glass Shard
6. Talk to All Cats
Sarah Lim (Likes Glass Shards, Flowers and Band Aids)
2. Feather
3. Reach Intimacy Level 2 with another cat
4. Find Her Key
5. Flower
6. No Quest
Michelle
2. Give her food back to her
3. No Quest
4. Talk to all Other Cats
5. Band Aid
6. Glove
Bobby Kim (likes flowers and band aids)
2. Flowers
3. No Quest
4. Reach Level 2 with Michelle
5. Rat
6. Band-Aid
Doggo (likes Leftover Fish, Big Fish, Canned Food, Rats, Glass Shards, Flowers)
2. Flower
3. Bone
4. No Quest
5. Talk to All Humans At Least Once
6. Reach Level 2 With All Humans
Gregory (likes Canned Food, Big Fish, Flowers and Band-Aids)
2. Find His Key
3. No Quest
4. Find His Wallet
5. Flower
6. Talk to Simon
Simon (Likes Band Aids and Big Fish)
2. Talk to All Other Cats
3. Glass Shard
4. Band Aid
5. No Quest
6. Talk to All Other Cats
Boss Cat (likes Big Fish, Canned Food and Rats)
2. Canned Food
3. Canned Food
4. Talk to Elder Cat
5. Rat
6. Big Fish
Freckles and Dotty (likes Big Fish, Leftover Fish, Flowers, Canned Food, Rats)
2. Glass Shard
3. Leftover Fish
4. Rat
5. Big Fish
6. Flower
I do deviate from this depending on how much time I have during sunrise and sunset and again, if you have some spare time, try to grab something quest related before bed that a morning NPC needs.
I recommend following the route I take, but remember that it will depend on RNG if you get the items as luckily as I do.
0:00 Intro
2:18 12 days until becoming an adult cat
9:05 11 days until becoming an adult cat
19:25 10 days until becoming an adult cat
26:10 9 days until becoming an adult cat
37:34 8 days until becoming an adult cat
45:05 7 days until becoming an adult cat
54:39 6 days until becoming an adult cat
1:03:55 5 days until becoming an adult cat
1:12:32 4 days until becoming an adult cat
1:20:45 3 days until becoming an adult cat
1:29:35 2 days until becoming an adult cat
1:35:20 1 day until becoming an adult cat
1:40:27 coming of age day
I still recommend choosing a "best friend" at the end or you will end up with a bad ending
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