Help!, or, Post-Tax Stress Syndrome

So I’m that guy who waited until 9pm on April 17th to do my taxes. In my defense, the guy who was supposed to do them said they were in the mail and his voicemail has been full since this afternoon. But they’re done now, four hours after my wife dropped off two fat checks with extensions at the post office (not to be confused with two fat chicks with extensions). Which brings me to my first question: should I wait until the IRS receives my mailed extension before e-filing my taxes, especially since I declared that I had already paid them all with the extension?

The second question doesn’t quite hurt the brain as much. I’ve been using Blinksale now for several months to track client invoices; and as much in love with the interface as I am, I realized tonight that I need something to keep track of business expenses, receipts, etc. I found several really nice looking programs for the Mac, but they deal primarily with project tracking and invoicing. QuickBooks looks great, but I almost think it’s overkill (and expensive). I really wanted to get Quicken Home and Business, but they don’t make it for the Mac. I don’t want overly complex (i.e. payroll) and yet I’m afraid Quicken vanilla might not do the trick.

Anyone out there in a similar situation got some pointers for me?

(Oh, and if you find something broken around here, don’t worry, I’m in the middle of spring cleaning…)