At Host Metro you pay $1.84 per month and this site is rated 5 stars in the community so it should be reliable. This is one of the cheapest Web Hosting sites on the web.
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My main question would be the level of security and confidentiality with an email hosting service in Milwaukee or elsewhere.
IMAP hosting can be found at several different places. Websites such as Siteground, Rackspace, or Neomailbox would probably be good places to start. There may be others that would be better for your needs.
Exchange hosting services provides a copy of the data on the client machine as well as a copy on the server itself which provides immediate backup of critical data. Traditional hosting services would require a specified backup of the client data be initiated to provide the same level of data recovery in case of a crash or corruption.
An example of a web hosting provider that uses Windows 2003 dedicated servers would be CrucialIP. They also offer many other dedicated servers at competitive prices.