Should I upgrade to the new firmware?
I have many things to consider one been I use my ITT at work...
What do you guys think?

its not essential. I only upgraded since I wanted to start using my device from my new 8GB SD card so I could fit and run all my utils on my N800, so it just made sense to try it with the new firmware, as well, I occasionally use skype(not sure if you can install it from old firmware. If you have the time to reinstall all your apps/utils and ssh everything back to your liking, then do it, everything that I ran on old firmware runs perfectly on new firmware such as python, ruby and utils. I havn't had any bugs. If not already I highly recommend you use a SD Card for OS boot. I used ext2, haven't tried ext3 for my OS.

Thanks for the info and advice I do have dual boot right now.

I upgraded when it became available, primarily for Skype and secondarily for SDHC-support out of the box.
I haven't had any problems whatsoever, I even restored my backup in the full. Everything is good.
However, as it turns out there seem to be a problem with the SDHC support (see other thread), so I'm holding back on new cards for now. So, what I gained was: Skype, even better battery (by a small amount), improved flash. What I lost: Nothing. If you don't need Skype, and youtube isn't important, then one might as well hold back though.

Do you want Skype? There are bug fixes too, the onscreen keyboard doesn't appear to mis-read as many taps now, scrollbars down the right-hand edge of the screen work better and the scrolling on the applications menu is much better when in "thumb" mode.

Oh, and the "Home" hardware button now pops up a thumb-friendly application switching menu, rather than a tiny and impossible to use one.

Make a backup, make sure it works, and then write down all the applications you have installed. This is the only problem with updating the software in your IT.

Well I'm a techie, so I like updates and am probably biased that way

I would say that the update is worth it for the touchscreen sensitivity fix alone. There's pretty much zero reason to stay on older firmwares.

Maybe if you like your memory cards in working order?

Maybe don't damage them by doing dumb things like turning off the device while files are being written or removing a card until it's not in use. 99% of the time, it's the reason why SD cards are damaged and I don't really see anything different this time around.

Being that I have no problems with my memory cards I must agree with this statement. I DIDN'T make a backup, I set aside about an hour to do the upgrade, wrote down all my must-have apps and then did the upgrade. I installed python first and then everything else. I have had minimal (read as no) problems and the touch screen sensitivity is back to highly acceptable standards. An interesting side effect of this is that I even attempted handwriting recognition and it 'almost' works now as compared to useless before.
I use my N800 in pretty critical situations and have had yet to experience any breakdown.
Do it!

I would upgrade primarily for the new beta browser.