If you believe his observations about the differences between free and paid sites, it would seem very difficult to reconcile them into one freemium site. You'd essentially have two tiers of users, with separate pools of personals and at least some variation in design.

Another challenge for PoF is reconciling their business models. AFAIK, right now PoF makes its money from selling leads to premium dating sites. If they're going to run their own premium site, doesn't that risk cannibalizing that business?

I don't always believe everything he says but he does sometimes make some good points. He says he makes his money entirely off google ads but then again he said everything runs off varying numbers of servers (it varies according to which article you're reading, sometimes it's "it's only 2!", sometimes more and on articles like this one: http://highscalability.com/plentyoffish-architecture mail servers and such aren't even mentioned) so I find that very fishy.

These assumptions he makes about free vs paid are reasonable but it's probably just a gut feeling guess.

If you actually look at pof it looks like garbage. No one would want to pay to have their photo resized so terribly and have basically no features. When you're paying for a service you have an entirely different set of expectations. pof works because it has a very large user base. That's all you need for a free site to work. For a paid site you need quality and he's famously very lazy so that's why he's looking to buy one instead of actually getting to work to build one on his own.

It's possible for a dating site to work on the freemium model. It's isn't for pof though, not without a lot of work he isn't willing to put into it.

I think he's going to find that the only ones he'd want to buy are the ones that aren't selling.