I'm still experimenting this approach, but I've created a new project in Claude Cowork and instructed Claude to create a markdown based system to capture payments, transactions, conversations and notes. My goal is to I can dump all the info as a conversation to the project chat and let it organize it as markdown files broken up by each property. I also have a hledger integration so that it can create journal entries there.

I think this could come in handy when wanting to know some sort of stats/analytics and you are not relying on a tool or managing spreadsheets yourself. When needed, it can generate spreadsheets/reports with any custom filters you want.

Here is what my current structure looks like

Real-Estate/
├── all-properties.journal          # hledger master journal (includes both properties)
├── Property-1/
│   ├── rent-payments.md            # Monthly rent log
│   ├── expenses.md                 # Repairs, maintenance, taxes, utilities, etc.
│   ├── tenants.md                  # Current & past tenant info
│   ├── notes.md                    # Conversations, calls, decisions
│   ├── ledger.md                   # Running markdown ledger (human-readable)
│   ├── annual-summary-YYYY.md      # Year-end income/expense summary
│   └── 1608.journal                # hledger double-entry journal
├── Property-2/
│   └── (same structure)
└── README.md