Building a community w/ email addresses

Hello again! I'm getting such great answers on this board today I thought I'd fish for some more. (For the future, can someone please tell me what would be most appropriate sub-forum in which to post this quest question?)

My site has about 2,000 loyal registered (and who knows how many unregistered) readers and users who are serious hobbyists and academic/professional type people who literally breathe eat sleep and breathe music. I'm thinking, as a way to encourage "donations" and generate some extra money, that I would like to start selling e-mail addresses from my domain as a yearly subscription type thing. Help me shake this one out:

Positives:
1. Community Building and improved word of mouth/name association
2. Extra cash

Negatives:
1. More to fix if something goes wrong
2. I'd have to support problems

Questions:
1. How much would you charge? $20/year?

 

Can you really do this anymore? Is your domain good? So many places have free domain things that paided things would be harder to get.. BUT, it would be a nice incentive to get people to donate so:

1. I would charge $15, to many free services out there (http://www.mail.dimensionet.com is my one)

You should consider how many people you can handel.

 

Don't try to sell a free email account.

Limit the registered users slightly and give donators a little more. Give them a private members only forum or two and throw in the email addy. Some may not want or need it, less management.

Sell them on supporting your common interest so your site/community can continue.

 

Would you be able to market any affiliate products to your registerd users? I personally think it would be too much of A hassle but again I am still learning.