If your provider won’t install for you a mod_rewrite equivalent for IIS, then you got to use permalinks of this form:
domain.com/index.php/about
Not very fancy, but a lot better than domain.com/?p=123
I don’t think you can get a solid answer for plug-ins. Just setup a test machine similar to your hosting provider’s and test all the plug-ins you are about to use, before you build the new wordpress site on the real server.