Scott,
Quicken Basic has options for: Banking(checking and credit cards),Investing,Property, and Loan accounts. You can also schedule bills and other transactions. Quicken won't pay them(bills) itself, but with online banking you can set the bank up to do that.
I don't track my retirement stocks that much as I work for the State of Ohio and they track all that. So I've never really used that opition.
However, I don't see how it would be that hard to run a small biz or your own IRA's with the Basic. You'd have to do some of the tax stuff for payroll and such yourself. Unless you deal with a fixed income, then just set it up once a year.
Heck, I havn't even had a checkbook in two years.

or bought stamps except for xmas cards. I do everything online.
Cost to me for all this: $4.95/month bank fees.