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It seems to me the more uncertainty there is, the faster you would want to recoup your investment. With today's climate, you could buy a website today and be out of business or in jail tomarrow.
If I were buying a website I would not pay any multiple for the monthly profits.
The only way I would buy would be an assets-only purchase. I would buy the domain, the content, the site design, html, scripts, servers, etc and price each item separately and add it up. The seller can keep his corporation and all his liabilities. I don't want people the seller screwed over that he forgot to tell me about coming after me.
Assets-only purchase is the only way to buy a business.
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