I am a noob with Silverstripe but decided it was the CMS for me after evaluating a number of options.
Now I am working through the tutorial and need to edit the page.ss file. Problem is, I'm mac. I was able to open on an old copy of GoLive once I changed the .ss to .html to make the code additions. I saved, uploaded it back, changed the file name back to page.ss, and then reloaded the page with ?flush=1 at the end of the url. My changes are not showing up.
I'm developing on a mac as well. I'm using eclipse, but if you never used it before, it might scare you a bit. There's an eclipse based IDE, specially designed for Web Developers called Aptana (http://aptana.com/) which might be worth a look. Also check out this wiki page for a list of possible editors: http://doc.silverstripe.com/doku.php?id=tools
I found Aptana's very un-mac-like interface infuriating. That and its clipboard handling is inconstant. Some data will copy and paste from/to certain apps while other doesn't. I just use Coda and MAMP, unfortunately Coda is't free. Its similar to SubEthaEdit which is much cheaper