The Pitfalls of Webmail - Part 1

I hate webmail. Hotmail, Yahoo! Mail . . . even Gmail, too.

I have about 7 email accounts that have accumulated over the years and I like having them all synchronized in one place. As a side note, I prefer Outlook 2003. Here are some reasons why I hate web-based email:

1. Space Limitations: so what if Google is giving me 2 gigs of space. Most of the emails I get are HTML based, which take up a lot of space if you don't want to delete them. With Outlook, you can keep your email server free from clogs and have everything locally.
2. No visiting multiple webpages: people sometimes have an email address from work or school in addition to one or two for personal use. I'm not logging into multiple sites just to check my email. The fix to this problem is to just have all of your email forwarded to one address (but see #3).
3. Identities: even if you forward all of your email to one central webmail location, it is difficult to reply from the address of your choice. If you are in Gmail and you want to reply to a message sent to your Hotmail address from within Gmail, your recipient will see the message as from "JDoe@gmail.com on behalf of JDoe@hotmail.com" which is frustrating.
4. Calendar and Contacts: many businesses and individuals want a sophisticated calendar and contacts management system because they depend on it to keep themselves up to date and propose new meetings. Webmail is not tightly integrated with any calendar applications, so kiss it goodbye.
5. No advertisements: I want to read my mail in peace and not be bombarded with popups or banner ads when I am reading. I would say privacy is an issue, but I doubt that my mail is that much more private in Outlook as compared to webmail.
6. Archiving: what happens Gmail is no longer the hottest thing and you want to change accounts a few years from now? How are you going to forward that mail? If you sit there and forward them one-by-one, not only will this take a lot of time, it will also permanently alter your To, From, Date Sent, Date Received, and Subject lines. This makes it very difficult to organize your mail later on.
7. Starting Over: even if I decide that I want to start using Gmail, how do I import all of my existing Outlook email into Gmail without losing my ability to categorize and cross reference emails? I've seen a few hacks, but they all have drawbacks. And again, if I forward my email one by one, I have the same problems listed in #6.
8. Integration with Microsoft Office/Adobe: this is very helpful when you want to send out documents for review constantly and want to keep track of them. Dragging and dropping attachments is a lot easier than navigting to them through some half-assed attachment menu. Note: Yahoo! and Hotmail have promised drag and drop functionality in an upcoming release.

I think issues 6 and 7 are the most important to me. To have no effective way of exporting or importing email in a number of different formats is a deal-breaker.