[Mark Rejhon]

In answer to your questions:

1. Problem: Web is not usable (too slow)
   Solution: For the fastest BlackBerry web experience, you should make sure you have one of the newer 32 megabyte BlackBerries. You should install the third-party Reqwireless Webviewer from http://www.reqwireless.com ... which is usually faster than the built-in BlackBerry browser. In general, thids web browser is much better and faster than the Hiptop/Sidekick browser, although you may need to turn off a few features to minimize download bandwidth.
   
2. Problem: Email only holds 6 megs
   Solution: There's 10 megabytes in most BlackBerry accounts, but you can usually request a free upgrade to 25 megabytes. Alternatively, you can purchase unlimited email space using a third party BES/MDS hosting provider. For more info, see Hosted BES FAQ.
   
3. Problem: Cant do much with attachments
   Solution: BlackBerry on BWC now supports PDF, DOC, XLS, TXT, JPG, PNG, TIFF file attachments. The BWC will convert it to a fast-downloading format, like downconverting the JPG to a smaller size. You can even have 1 gigabyte of images and you can still download them on demand through your BlackBerry. Recently, you are finally now able to view images on BlackBerry without needing BES. And even better, if you are a power user, you may become interested in a free software program called "eFile" from Dynoplex that provides a filesystem for BlackBerries, if you like to copy images back and fourth over the USB cable.
   
4. Problem: Not enough applications to keep me busy
   Solution: You're in luck! During year 2004, the BlackBerry software market exploded, and now you have over 1,000 applications compatible with BlackBerry. Some of my favourites are listed in BlackBerry Killer Software thread, BlackBerry PowerToys thread, and you can even install Nokia, Motorola, Siemens, SonyEricsson Java midlet apps on a BlackBerry nowadays!
   
5. Problem: Security issues with T-mobile
   Solution: You're in luck! BlackBerry is one of the safest mobile platforms available, and if you are using BES within your company, your email/PIM is always encrypted all the way between your company and BlackBerry during wireless PIM sync. No worries about Paris Hilton and her stolen Hiptop/Sidekick addressbook! In fact, you can even stick with T-Mobile, since you will be bypassing their addressbook system.
   
6. Problem: AIM is weak (bounces on & off) plus its clunky
   Solution: It should now be finally better on BlackBerry than Hiptop. Verichat is a very elegant program that's very simple and non-clunky. It was not until recently that improved IM software has finally made BlackBerry a more reliable IM platform than a Hiptop/Sidekick (At least if you are using BES/MDS, which is more reliable than either BWC gateway or Hiptop gateway). When you use BlackBerry Verichat/WebMessenger, it's finally reliable enough to be used as an always-on device. Personally, I successfully ran Verichat for 75 hours non-stop. Great battery life too! There's always occasionally some reliability issues with AIM itself, and some carriers have lots of problems with IM software until you obtain BES/MDS Hosting, but the fortunate thing is that you have many options now (many brands of chat software, many options of improved networking, all major carriers now provide BlackBerry service, you can cherrypick a good service). For more information, see BlackBerry Instant Messaging FAQ.
   
7. Problem: 4 email accounts at once!
   Solution: BlackBerry handles this no problem. You can configure the BWC to do multiple email accounts. I can do up to 10, although I use email forwarding instead because it is much faster that way.
   
8. Problem: Auto grabbing emails
   Solution: BlackBerry handles this no problem. BWC checks email every 15 minutes (although this temporarily speeds up to about once every 5 minutes if emails are coming in very quickly). You can even bypass this by using email forwarding, then your emails show up on the BlackBerry less than 15 seconds after "SEND" on the other end. Or if you use BES on an email address, then you get speedy delivery that can even be less than 5 seconds after somebody sends it.
   
9. Problem: Email layout with various folders is nice
   Solution: You might come slightly short here, since this is usually a paid-extra service. The default BlackBerry software only provides a few folders. For a true folders system, including wireless synchronization of your Microsoft Outlook email folder tree, you need a BES, for more info, see the Hosted BES FAQ.
   
10. Problem: there are so many downtimes
    Solution: You'll be very happy with BlackBerry's reliability. Downtimes on the BlackBerry network is extremely rare, and if you are using a BES server, it actually sometimes never happens.
    
11. Problem: bulkier than Sidekick?
    Solution: That's not true. All BlackBerries are smaller than the original Sidekick I. Although a few models of BlackBerries are slightly bigger than Sidekick II.
    
12. Problem: How is the "web" on the blackberry, is it usable or slow as all heck & timeouts all over the place?
    Solution: It's very useable! However, BlackBerryOS 4.0 web browser is very slow sometimes until you turn off JavaScript and turn off Tables/images. Or you can use a third party web browser such as Reqwireless WebViewer. I have never had timeouts on Rogers, although I heard T-Mobile is sometimes overloaded, so I might prefer to go with Cingular 7290 or Verizon 7250. Try a Cingular 7290 first, that has longer battery life.
    
13. Problem: Any ideas if I would be happy making a swap from the sidekick to the blackberry?
    Solution: According to your needs, I think you'll wish you never purchased Sidekick - All the needs that you listed, can definitely be met.

Just be careful about which network you get it on, because some of the networks are much better and faster (i.e. Cingular). T-Mobile has better coverage in some suburban areas I have been in, but Cingular has a bigger coverage footprint, and I found data to be generally at least twice as fast on Cingular. I am on Rogers and am able to roam on both T-Mobile and Cingular, and the roaming seems to work better on Cingular. If Cingular is TERRIBLE in your area, you should try something like Verizon or perhaps AT&T (Cingular Blue). Nextel is GREAT but you won't be able to do SMS/text messaging very well on Nextel. There is NO "perfect" carrier, but Nextel is great if you can forgo outgoing SMS messages. If you must use SMS messages, try Cingular. Cingular's network is much improved since the last 2 years, so I would give it a test again. Cingular and AT&T merged, and now the network is more-or-less unified, which makes the coverage much better than it used to be (although there were some merger pains in some areas). On the other hand, if you want to save the most money, a T-Mobile BlackBerry plan is usually the cheapest one to go for. (And I think if you are in California, the T-Mobile BlackBerry automatically uses Cingular's network!)