Can Outlook provide summary report information such as what percentage of my contacts live in California or how many hours I spent in meetings with a particular contact last month?
The closest you'll come to obtaining this kind of reporting directly from Outlook is through the grouped view. When you group a table view by a field, Outlook shows you the number of items in each group, but it doesn't give you percentages or totals.
My favorite quick-and-dirty reporting technique is to paste information from Outlook into a Microsoft Excel spreadsheet. Start with an ungrouped Outlook table view, then right-click the column headings and select Field Chooser. From the Field Chooser, drag any additional fields that you want information about to the column headings. You can also drag any column heading you're not interested in out of the view. When you have all the columns you want, select all the items in the view, then paste the information into an Excel worksheet, which will let you use Excel filters, pivot reports, and other techniques to slice and dice your Outlook data.
The Excel method is adequate for one-time reports, but it's not practical for daily reporting. You can use a linked table in Microsoft Access, but this solution probably won't support all the fields you might need. Consider a third-party general reporting tool (e.g., Crystal Decisions' Crystal Reports) that works with Outlook and Exchange Server data to produce detailed reports you can save for reuse.