Yeah... Outlook can be a little irksome, because it has evolved to do so much. But after reading your second response, you also want a lot out of it too, so you are kind of a power user.
First thing to understand, is that while people visualize all our email, contacts, calendar, etc. as separate items, they are as you note, all in a single Outlook.pst data file. Depending on how old your version of Outlook, this data file would go KABOOM at 2gigabytes, or 20gigabytes. In order to fix it, you had to run the outlook repair tool, which would truncate your data file, and lop off the overage, leaving you with random data loss.
What I would suggest, depending on your ISP and how much data you have, cost of online storage, and if upgrades are costly or not, is to download the Outlook backup add-in free from Microsoft, plus create new Achive datafiles with their own subfolders, separate from your main Outlook.pst and store the bulk of everything there except your active inbox, or...
OR... much much better still, (it will usually cost you 5 to 10 bucks a month, but may be worth it depending on how much you value your sanity) is get a Hosted Exchange account. The beauty of Hosted Exchange, is that your local data file becomes just a mirror of the online data file, and when you install your email on other devices like your smartphone, etc, your full email subfolder tree, calendar, contacts etc. look exactly as your desktop. You also get OWA (Outlook Web Access) which you can pull up your same email and tree, cal, etc. in a web view from any pc with a browser. Plus, it is backed up for you and mostly worry free with a good ISP. Many side benefits include the fact that your ISP will pre-scan for junk mail, spam, malware, virus, etc. You have much more control over email contact distribution lists, etc. as well.
One last tidbit. I can't tell you how many people "think" they have all their contacts stored, that in fact, do not. They have many cached email addresses they have previously typed, and are just memorized in something Microsoft calls the nickname cache.
In Outlook, this is similar to the browser form-filling autocomplete cache that remembers when you go on-line and fill something out that requires your street address, so when you pull up a web page next time and start to fill in out, AutoComplete pops up and fills in the blanks for you. This, in older versions of Outlook was stored in something hidden on your hard drive call an NK2 file. When people upgraded to Outlook 2010 and newer, the NK2 file did NOT automatically convert and people assumed they "lost" email addresses. Not so, they lost the cached addresses they previously typed, but never created contacts for. This NK2 file can actually be manually imported from your old PC or outlook hidden folder with a tool you can download for free from the Microsoft support site.
And that as they say, is the rest of the story.
Hope it helps someone,
EricV
Randy, I could almost write a book in response. 
First major problem has been "here today, gone tomorrow", requiring lengthy repair or re-install. Or, it seems to lose track of my contacts for a day or two.
Actually the biggest issue for me is the contacts. I have a huge number in connection with the eBay store and other activities. I use multiple email accounts, and Outlook wants to associate each contact with a specific email account. I move them all to a group in the Outlook data file, but then entering the contact into a "To" line on an email, for example, becomes a time-consuming search.
I've also sorted contacts by Last, First names for years. Outlook wants the full name on a single line.
After using Windows Live Mail and its much better contact handling, formatting options, yada yada, Outlook is a real bummer for me. We're also experiencing in recent months all too frequent "Internet Explorer has stopped working" messages on all 4 of our computers.
Dennis
Topic: Completely Off Topic: Email Software (Read 2775 times)