Red Dead Redemption 2

There are 7 homesteads, but you only need 4 caches. This way, you can choose from them only the ones you want to make. The last one, Willard's Rest, becomes available only in Chapter 6. You can collect the rest in Chapter 2, and it is recommended to do this early on. At the end of the game, some of the manor residents may no longer be there, meaning you cannot ask them around for clues. Or you may have already killed them, which will also complicate the situation.

Make sure you loot everything, not just the stash. This may be required for the trophy/achievement unlock to work.

Chaz Porter:
The cache is on the top floor of the barn. You go to rob this place with Javier when accepting his home heist mission in Chapter 2 or Chapter 3. Javier can be found at your gang's camp. You can still go to the manor without it later, but it is unknown if it will then count towards unlocking the trophy. Inside the barn, you can climb the stairs to the top floor to find a cache next to some haystacks. The chest contains 2 x $50 and a pouch of jewelry. Rob everything else in the houses too.

Aberdeen Pig Farm:
When you arrive at the farm, there is a guy sitting on the porch who greets you. Talk to him and follow him into the house. Then rob. Also be sure to go back outside and enter the door on the south side of the house. This will allow you to enter the room with the cache. This door is locked until you follow the guy into his house. Inside is a small safe with 2 x $20, don't forget to loot along with everything else in the house.

Lonnie's Shack:
There are 4 guys inside Lonnie's shack. Kill 3 of them, but leave one alive! It's best to do a manual save in advance. Point the gun at the last survivor and threaten him. He will tell you the location of the cache. This will be different depending on who is the last one standing. For example, the stash could be under the pillow of one of the beds or in a sack of grain in the kitchen, but unless you interrogate the last guy, you won't be able to take the stash.

Van Horne Mansion:
There is a villa south of the Van Horn trading outpost. You must go here at the beginning of the game. Enter at night (you can make camp and rest to pass the time ahead) and you will find two people sleeping on the bottom floor. Steal money from their table and loot everything else in the house. If you come here after completing the story, it is possible that you will not find either residents or money in the table.

Jackson House:
Enter the Jackson house. There is either father and son inside, or just son. You can take the shotgun from the living room and threaten your son to tell him where the hiding place is. It can be located inside the chimney or outside the house, on the side to the right of the entrance. There is a small hole on the side of the house with a box inside. Interact with the box and loot it. But be sure to loot everything inside, especially the premium cigarette packs in the son's room chest and the shotgun from the living room.

Watson's house:
You will find an old woman in Watson's house. Enter her house and use the stairs in the back to go down to the basement. Steal the shotgun and leave. Now set up camp and rest twice in a row to move on to the next day. Then return to the hut and you will meet the woman's 4 sons. Kill them all and the safe on the kitchen table will now be available, which was not there before. The safe is a hiding place and contains 1 x $73.00.

Willard House:
This is only available after completing the first story mission in Chapter 6. Go there and talk to the villager and tell her how to hunt. Return in 2 days (use the camp). When you return, have a shooting match with her, and then you can rob her safe. Don't forget to steal everything else too.

After you loot 4 of these 7 locations you will receive the "Breaking and Entering" trophy/achievement.

We will rob 2 caches at once according to the plot
I recommend watching the rest here - https://www.youtube.com/watch?v=LOC-IJSkwTc&t=415s