Email security is so important yet so few people even realize it. Gmail does a great job and always has with their SSL and they have many other minor features implemented to help prevent people from getting your password and if they do you can check the logs and should be able find out. Picking good passwords is also important. Not using the same password also helps as if they get one, many people will try the same password at other sites--including your email as so many people are too lazy to use different passwords. If remembering passwords is a chore for you try 1Password (if you are on a Mac).
Never use anyone else's computer and stay far far away from any Internet cafe as you can probably assume they're collecting your info. Use a VPN if using wifi if you are really concerned.
Yet I think your questions are more about your server. Make sure the location of you file is below your public files. You might wanna change your site/server passwords if you haven't done so in awhile as maybe someone has access. Password Sentry I think has an anti- bruit force plugin so check into that. I hear they're coming out with a major upgrade for that soon and I'm looking forward to learning what neat features it has built in.
Sniffing isn't something you can do much about as it's mostly on your customers end, but I'd doubt that's a major issue with people getting endless amounts of your passwords. I would say check your password file location, change your passwords, and look into bruit force prevention by checking the PS plugin.
Oh, one last thing, consider getting a monthly subscription to a security company. I use a company which for just $100 a month they make sure my sever is secure and they monitor it 24/7 and will handle issues and alert me when there is a problem. I also check with them first before installing different programs to make sure I am not creating a security hole--a few times they've even warned me against some programs and suggested more secure options and they'll even install them for me at no extra costs if I want.
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