Re: Stand alone mail program, or webmail?
I only use webmail for personal use. Gmail for business, yahoo for personal and another yahoo account for baseball stuff.
I have to use Outlook for work, mostly it's great for the calendar part, aside from that there is nothing else it does that I can't get elsewhere.
Used to use Thunderbird for work at my last job, it's alright, but doesn't play well with other folks Outlook accounts.