Test Five: Regular payments
Regular transactions aren't always exactly regular. For example, when a monthly payment falls on a Sunday, it may move to the previous or next working day. And some bills are always payable on the last day of each month.
Most of these apps can't cope with that variability. Money, MoneyWell, iCompta and Liquid Ledger offer a selection of regular intervals that can repeat indefinitely or end after a fixed number of occurrences. That's useful for things like loan repayments that are fully repaid after a set number of instalments.
However, none of those programs can constrain payments to working days or compensate for different lengths of month. FinanceToGo can't do it either, but it lets you define intervals, such as every third Tuesday.
Only Stash tries to break out of the strait-jacket. As well as the usual intervals, it adds Last Working Day of the Month and Exact or Next Working Day; still not flexible enough, but it's by far the best.
Test Six: Security
You won't need to enter account numbers or passwords into these programs, though some of them encourage you to do so. Avoiding this cuts down the risk of identity theft. Even so, do you really want all your financial transactions to be seen by anyone else?
A robust user login password for your Mac is the first step, but additional defences in the software would be welcome.
Stash has no built-in security at all, so it's up to you to encrypt the file if you want it secret.
Doing somewhat better are FinanceToGo, Money, Liquid Ledger and MoneyWell, which all provide simple password protection for your files. Ideally we'd liked something stronger.
Only iCompta takes this seriously by offering password based encryption. Give it a unique robust password, and your financial data should be impregnable.
Remember, though, that no amount of security can protect your Mac from being stolen or destroyed, so back up.