I'm on my work machine, which is running Windows. I'm pretty sure I can convince the boss to allow me to format and install Ubuntu so long as all the applications I need will work. The only one I think I'm going to have a problem with is Outlook. Is it possible to install Outlook on Ubuntu? If so, what settings should I make sure I take from Outlook on my current Windows machine before doing so?
It is possible, I used to do it with outlook 2000, but I don't think newer versions of outlook are supported in a way that is sufficient for professional use.
Depending on the way outlook is used in your company, you might prefer switching to evolution, which is what I had done initially. However, we use outlook as a mail client and have another groupware suite for calendar and tasks.
If you do not use an exchange server or if you have enabled imap on the exchange server you could use any mail client you prefer.
Generally, if most of the work is done on software running natively on linux a migration has good prospects. If you intend running most of the software via wine, I would not do it.