Quicken (and I’m assuming Quickbooks) allow you to attach receipts and other files/images to a specific images. The 2009 version has some improved support, categories and reports for rentals. I tried thier new “Rental Property Manager” but found it more suited for landlords with multiple long term tenants vs vacation rentals. Perhaps the next version.

Evernote http://www.evernote.com/about/what_is_en/ this may be particularly attractive to folks with PDA/Smartphones, while it lacks the targeted features of shoebox.

BillPay I highly recommend using electronic billpayment for almost everything that you can’t use a credit card for. I found ING’s Electric Orange account ideal for me as it’s FREE with no minimums and provides interest on your checking and a linked high interest money market available. http://home.ingdirect.com/

Andrew