I don't have personal experience of high end escorting but my attitude is, if you're in the right shape and age group - go for it! And if you're
not in that model look shape or age group - then go for it anyway!
The only "bad" thing that can happen is that you don't get enough clients. And if that happens you can always re brand yourself with new pics, name, site, mobile phone and start afresh in a different price range. Or even run both sites simultaneously, targetting different markets.
Sure, there could be grunts from certain punter sites "exposing" you as same escort. But then other professionals sell their services at different prices to different markets too (and no one bats an eye lid). Besides, how many well off clients actually read Grunternet?
So you may get arrogant wankers? I'm sure they come in all income brackets. So clients expect more "services" (read: you taking more health risks) once they pay more? I'm sorry, but I don't buy this argument. Truth is some men will
always expect more whatever your prices. And IME there is far more pressure to perform OWO & the rest in brothels, for much less money than what many agencies and independents charge.
The only downside I can see is the need for a Posh PostCode Luxury Flat (for your in calls) which sure hell could eat into your earnings. But if you manage to share a flat with others then I think it could still be worth it. I am currently tempted to advertise in Cherrygirls and Eros with my (medium priced) site. Both directories have quite a few VIP escorts advertising there. Which is why I get a feeling that if you're looking for well off clients, then my only advice would be to pay a bit more to get listed on well established smart(er) directories (with good results on search engines). Hopefully the ones which your desired clientele is most likely to find when searching for escorts. With other words, not at AdultW**k.
And if you're really daring you could contact other VIP escorts to see which advertising has worked for them or not.
One piece of (on line) advice I've got from a semi retired Courtesan was that if you're charging thousands of $s, then you may only get 1 or 2 clients a month - if even that. It takes time to build up a network of clients on that level (and since she already made money elsewhere, a booking like that was more like an icing on a cake as opposed to her main income). It also seemed to involve longer dates as opposed to 1 hour bookings.
And oh, she claimed that even to this day and age it was possible to have $5000 overnight stays without even kissing your clients (at least in US). Pop goes the argument that the more they pay, the more "services" they'd expect. According to her, it wasn't so much of what you did that mattered, as to how you chosen to
be with your clients. Personally, I believe it to be true. Sex is after all not just a list of things you do, as much as an event you both explore.
And I think there are quite a few men prepared to pay more for quality as opposed to mere quantity when it comes to sex. As to whether it's enough of them to go round, that's a different story.