Twenty five or years ago I was the youngest banker in the commercial department of a regional bank. I handled all of the walk-ins, many presented with situations like yours and asking similar questions. I had a few pat questions for them. The first was, "why would you want to be in business for yourself?" No offense, but a response along the lines of yours, "I like the idea of being my own boss," was usually a red flag. It was a window into naivete that anyone who's been in business for themselves can educate you to: if you're in business for yourself, everyone is your boss! The second (or so) question was, "what would it cost you to start up this exact business from scratch?" That would help us back into the amount of goodwill in the purchase (the value of the business as a going concern). Then we'd discuss whether or not the business was actually worth the premium asked over the value of the assets. You'd be surprised how many times this was the end of the conversation: they'd never thought of the transaction in those terms. Getting past those points, the conversation generally moved toward evaluation of historical financial information of the business and the prospective buyer: could the business be expected to provide income sufficient to support the buyer's lifestyle and how much stress could be placed on the business (interest rates, economic downturns, reduced revenues, etc.) before the buyer's lifestyle was at risk? Specific to your situation: it's been years since I fielded an opportunity in print media and I don't know your market, but my perception is in line with the concerns expressed above. That said, there are always ways of making money in waning industries, but success hinges on getting in at the right price and running it with a mindset that the profitable timeline is probably limited.