Honestly, all personal budget systems I've tried are crap.
I use two systems:
1. Annual budget spreadsheet. A simple high level of what my planned income is and what my planned expenditures / investments are. If there's anything fundamentally wrong about my plans, it's caught here.
2. GNUCash for transaction history plus 90 days of forward looking planned transactions. If there's a projected account shortfall, I can rebalance accounts, and determine whether this is a temporary cash flow problem or if I need to adjust my annual budget.
This setup works fairly well for me, though a tax accountant will still be useful in navigating things like what is and isn't a deductible expense, what documentation is required, and how to adjust your future plans to become more tax efficient.
I found YNAB to align the most with how I think about budgeting. Zero-dollar, category based that only focuses on the amount of money you have now and not to worry about cash forecasting. However, your description sounds like you need a bit more of an accounting and budget application than a strict budget.
I use two systems:
1. Annual budget spreadsheet. A simple high level of what my planned income is and what my planned expenditures / investments are. If there's anything fundamentally wrong about my plans, it's caught here.
2. GNUCash for transaction history plus 90 days of forward looking planned transactions. If there's a projected account shortfall, I can rebalance accounts, and determine whether this is a temporary cash flow problem or if I need to adjust my annual budget.
This setup works fairly well for me, though a tax accountant will still be useful in navigating things like what is and isn't a deductible expense, what documentation is required, and how to adjust your future plans to become more tax efficient.