What is the hardest thing about managing your finances? So many aspects to your finances, whats are some of the challenges you guys have?

Predicting and ensuring future income.

Most of financial planning assumes you're employed during that period of time. But if you're unemployed and not due to illness (because insurance can cover that), but more due to retrenchment or being obsolete, then it's definitely an issue.

The last thing is also expected rate of return of investments. The biggest issue is time. You can't reverse time if your rate of return wasn't enough to achieve your goals. Once time has passed, you have to accept what you got. You can't also try to take more risk at an older age to try and make up for lost time, that's how you lose more money.

So income and required rate of return are the 2 biggest issues to guarantee will be there/sufficient.