color me pedantic, but it bothers me when i see professional communications coming from hotmail/ yahoo / gmail...

on the other hand i am far less annoyed by a gmail address than any other.

and on the third hand, given that gmail will host you for free, and your only expense is the domain name (which is about $2/year) so how cheap / inept / un-savvy do you have be not to have branded email?

as for changing email addresses mid-stream, that bothers me the most -- email programs are designed to auto-extract names & addresses, and having multiple addresses just clutters my address book and leads to confusion when i want to compose an email rather than reply to one.

I also think that it matters. I work for a steel trading company and receive frequent solicitations from overseas by e-mail. I feel much better when the e-mail is not from an aol, hotmail, yahoo or g-mail account in the beginning for sure. Once a relationship is established, I become more comfortable with someone using a different account or personal account. But establishing a relationship for me requires regular performance over the course of months and years because it takes so long to produce and ship the products that I'm interested in purchasing. If someone sends me an e-mail from 5 different accounts during the initial "get comfortable" stage, I start to think that I have to worry about them running away if there is a problem or being stable.

I also agree with Michael's comment that it is irritating to have to think about multiple e-mail addresses for one person when I'm dealing with hundreds of people on a regular basis. If I ask a secretary to send an e-mail on my behalf and she hits the one that my supplier forgot to check that day, it could set me back a whole day in many cases.

You can always set your "From" address on your various e-mail programs to jeremy AT jer979.com. You can do that with most e-mail programs I can think of - certainly with Outlook and G-mail, at least.

Agreed, though, with both of the above - having multiple addresses is mostly confusing when I want to send an e-mail to that person.

Yes, it does. Especially if you have a small company and are trying to build a brand. If we remember the 3C's, clarity, consistency and constantcy, then the email you choose to use is a big part of that.

I think it does matter. If I am corresponding for business purposes and the other person switches to gmail or aol I would feel like it has become "personal." It could also be a sign that the person is planning to leave the company.

I also think that it appears very different when someone sends you an email from a company email address, and one that has an actual website of the same name that I can check out. I am much more hesitant, when I don't yet have a relationship with someone, when I see that their email is coming from a free hosting source. It feels much less stable to me.

I also get confused when people are using multiple email addresses - how do I know the best one to use to reach them? Send something to all of them, or trust they are all being seen wqually so taht any one of them is fine?