What are the best practices with using a service which has a one button wordpress install. Install wordpress with one button install on web hosting servers?
I have such a service (installatron) running on the webserver of my hosting comapny and I like it a lot. It installs the latest version, is incredibily fast ( a few seconds for the complete install, really), handles the database settings for you (it creates a database on your server, a database user and password) and it even handles the safety settings correctly (like setting sufficiently secure "secret keys" and passwords etc). Remember to print out the mail you receive with the passwords and database settings and keep it in a safe place. Not all services are as good as this one though, so check that out first. (or later, you can always do a re-install later) Also check if the Wordpress install is the latest version.
Is there a way to sync with your site that you can work on the live server? I noticed everytime i seem to add my server it will connect but never sync with a new site / server. Test Connection Link's though.
Yes, you can work on a live server if you set up your site correctly from the Site/new site or Site/manage site menu in Dreamweaver.
You can also GET the remote site and keep it on your own computer, but you won't see anything happening if you make changes since Wordpress needs to run on a webserver running PHP and MySQL. You can also work locally and upload the changed files to your remote server using PUT from the Files window. You can even do this automaticaly by checking "automatically upload files to server on save" from the advanced/remote info tab in the Site Definition window.
Am I going to be forced to install / purchase mamp to more easily create install's of wordpress?
If you want to run Wordpress on your own machine, for development and testing purposes you will need to run mamp or wamp so Wordpress can run.
If you want to run Wordpress on a webserver you won't need it. Dreamweaver or an FTP program and a texteditor is all you need.
Firefox and the webdeveloper plug-in (of Firebug) is also very handy, check that out.