classified ad software and web hosting

I’m interested in starting a classified ad website. There is a lot of software to choose from and a lot of outfits that will host it.
I’m at a lost a which way to go, should I hire the host or invest in a serve to host it myself. After several months of membership a TechRepublic, I realize how computer illiterate I am. So, I asking any of you Pros, is there any one out there who can lead me in the right direction?