if you go the linux route you cant use any of microsofts .NET technology because that is designed for windows. There is something called Mono that is supposed allow you to use .NET on linux or something, but i'm not really interested in that - if microsoft cant be arsed to make technology for everyone then i cant be arsed to use it.
As for front page extensions you would loose all credibility if you used them in your website anyway and they are one of the main security holes anyway.
Those are the only two things that i can think you wouldnt be able to use, but obviously there is the issue of have you ever used a linux based operating system before? If not there are going to be some things to learn along the way but you'll be glad you did and most linux distros make it very easy to get apache up and running.