When Websites Outgrow Their Webmasters?

Seumas asks: "Like a lot of other people (especially at Slashdot), I run a Web site which is growing fairly popular. Sure, it's no Slashdot or MP3.com, but, it is growing so large that I can barely afford to continue paying for it out of my own pocket. In my instance, I have a specialized auction site with over 6,000 members and page-views in the millions-per-month (the site has only been around for a little over a year). What was started as an excuse to learn Perl has turned into a project that eats up my money, time and patience. So how does one make such a project pay off...or at least, pay for itself?" I realize we may have covered such issues in other past Ask Slashdots, but the fact is, many of you who run Web sites may find yourself in this position, and the more answers and testimonials I can get from those of you who have already gone thru this, the better things will be for those who follow.

"Does one soil their site with banners? If so, who pays out without requiring a percentage of click-throughs and who doesn't welch on their payments? Do you forego advertising and charge members directly for a yearly subscription to your service? Do you let users bankroll their accounts and then draw from their credited monies each time they use your service? How do you strike a balance that allows you to keep funding the site and not drive your users away?

Finally, who do you go to when you realize you can't do everything yourself? Is there anyone you can trust to acquire advertising, funding, a business-plan and other necessities of a growing online organization? I don't want to lose a good thing simply because I wasn't a business major and didn't know who to call when the job required more than one part-timer (me).

For me, this was never about money and it still isn't -- I just don't want to go broke trying to fund a 'hobby'."