I've been using Moneydance to manage my personal finances since around 2004. It's a great package. It can also track investments. I created a portfolio for physical PMs and cryptos. It's not perfect, but it's pretty good.
*edit: spelling *edit: removed screenshots
I'm a big fan of MoneyDance. It's a Java app, so it's interface is not 100% Cocoa compliant, but for a Java app they've done a good job of trying to fake a proper OS X interface. I really like it's home screen that shows me the balances of all my accounts, a calendar with my bill reminders on it, a separate reminders section with the next two weeks of upcoming transactions, and also its ability to download transactions directly from my financial institution.
Also, there's a free iPhone/iPad app that automatically syncs whenever it sees the desktop app on the same LAN. You can use this app to record transactions and look at history while you are on the go.
I think they charge $40 for the program and they have a strange demo- you can manually input up to 100 transactions before you have to register. This is kinda weird because you can import as many transactions as you like- which for the complete cheapskate could mean just entering transactions in a spreadsheet, saving as .csv and then importing all the time. I think it would get old, but it could be done. I found it to be worth the $40 price tag.
Been using it since 07/2008 and am very happy with it.
EDIT: I forgot to mention the "Expenses" tool on the app's home page that provides instant, reporting drill down.