One highly recommended personal finance and investment app that meets your criteria is Quicken. Quicken is a comprehensive personal finance software that allows you to manage your finances, track investments, and monitor real estate in different countries. It offers automatic transaction categorization and allows you to create rules to categorize your transactions automatically. Key features of Quicken include: Automatic Transaction Import: Quicken supports automatic data import from your bank accounts, credit cards, and investment accounts. This helps in eliminating manual data entry. Customizable Rules: You can create custom rules to categorize transactions automatically. For example, you can set rules to categorize Starbucks transactions as food expenses. Investment Tracking: Quicken provides robust investment tracking features, allowing you to monitor the performance of your investment portfolio. You can set benchmarks and compare your investments against them. Real Estate Management: Quicken includes features for tracking real estate, making it suitable for your needs in managing properties in different countries. Offline Access: Quicken is a desktop software, offering offline access to your financial data. This addresses your concern about security, as your financial information is stored locally on your computer. Trend Analysis: The software provides tools for analyzing trends in your spending, income, and investment performance. This helps you make informed financial decisions. Keep in mind that while Quicken is a robust solution, it's always a good practice to regularly update the software and follow security best practices to protect your financial information. Before making a decision, it's advisable to check for the latest reviews and features to ensure that Quicken or any other software you choose aligns with your specific requirements.