Answer: Using your own server is like having your own transport system. You must have really good reasons to own a bus, maintain it and be sure of what to do if something goes wrong. It’s much better to just hop on a bus owned by a transport company.
Do what you do best. Don’t get into areas where you need a whole bunch of expertise and are setting yourself up for chaos somewhere down the track.
Question: You mention that I should get a website that easily updateable. What are your recommendations?
1) Get a designer to build you a database driven site
2) Get yourself a site in Dreamweaver that you can update
3) Get Mambo and learn how to use it and you should be fine
My Personal Experience:
Learn Dreamweaver if you’re serious about Dreamweaver. You can’t go wrong with it.