Like you, I spent years struggling with PC-based email. Outlook, in multitudinous versions: Outlook Express (which isn’t anything like Outlook itself), Windows Mail, Windows Live Mail, Thunderbird. I can’t recall how many months I’ve lost trying to hassle with files, settings, quirks, and bugs.
Bah! If you haven’t yet moved your mail to the cloud, it’s time to take a look. Although you have to jump through a few hoops, it’s relatively easy to keep your email address (firstname.lastname@example.org) and push everything through Gmail -- and nobody will know the difference. All of the email services are free for personal use and come attached to more expensive packages (Google Apps for Business, Outlook 365, among others) for organizations.
Flipping to online email will add years to your life. The only real question is which service you should use. The two front-runners, Gmail and Outlook.com (formerly Hotmail) have pros and cons, with features in one showing up in the other sooner or later. Both have so many capabilities that nobody uses more than a tiny fraction. There’s no clear winner.
Personally, I use Gmail -- and have for years -- because it’s better organized (which is a simple way to say that I’m used to it), it does a better job of trapping spam headed my way, separating “Important” messages from “Everything else” simplifies cleanup, and the tabs help occasionally. Microsoft counters by saying Outlook.com doesn’t serve ads targeted based on email contents (although they do serve up targeted ads), they have inbox organization by custom categories, there are time-based rules, and Outlook.com makes it easy to connect to Skype, Twitter, Google, and LinkedIn.