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Checking the legalities where you live will be the single most important thing!
In most EU countries, running escort directory, blog, ad site etc is perfectly legal and you can even use paypal for payments!
How to monetize - have a way to let ecorts and ecort agencies in your area promote their service and charge for that
It's a small market but there is money in it, the girls are always looking for new clients and if your website is bringing them business they will be more than happy to pay
In US this is a lot more tricky and you can easy end up being charged with facilitating, but in EU it is more relaxed (that's why you can even use paypal), in some countries prostitution is even perfectly legal, so don't listen to people in US (or do this in US...)
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