There are millions of hookers and johns in this country, LE isn't going to be hacking my e-mails to see if I am talking to hookers. I also have no boss, no wife, no kids and no one who is going to be shocked that I patronize hookers.  

So, no I wouldn't pay a single penny to be able to hide my whore mongering proclivities, If LE is going to go to those lengths to ensnare hookers and johns, just reserve my prison cell now as it's going to be a  very full house. lol

unless you are a major trafficker.   We generally don't rate enough for LE to get warrants, etc. to make a bust.   They can get all the busts they want by planting a BP ad, and sit waiting for the johns to come rolling into the Motel 6.

 
On the other hand, if you are in a divorce, you better believe that your wife's lawyer is trying to find dirt on you by having a detective snoop into your life.   In that situation, it is probably best to just sit it out and wait for the divorce decree.  I'm not saying it will hurt to use the methods you suggest, but it is a complication, and just not necessary.

**They're not concerned because no one is after them**.
It's like asking, are you preparing for a North Korean missile strike? You could go out and build a blastproof bunker in your back 40, stocked with rations. You could setup early warning radar to  know when to use said shelter. You could even move your entire life to that shelter so you'd always be ready.  
The fact is, North Korea isn't gunning for you, so you're not really any safer than before you started. The boogeyman is in your head.
 
The vice cops aren't reading your texts and emails simply because there are plenty of idiots to mop their quotas with on backpage. They post a couple ads with maximum ~~~|||\~||\\\~|||~|~ and a low rate, setup a sting and rake in 30 guys at a time. This is simple, low cost, low effort and makes them look effective to the folks that expand their budget/salary/pensions.
Once in a blue moon, they'll go out and try to find someplace that's actually trafficking people and bust them. This is mostly for the publicity, not so much because they actually give two shits about it. They're really like every other government wage slave. They're just putting in their 20 years with as little work as possible, then retiring and collecting pension. When you start framing things correctly they make more sense.

So to answer your question, would I pay more? Hell no. Would I be happy to have more security, so long as it was unobtrusive? Hell yes. Signal messenger would be great, signing everything with PGP and using one time pads is overkill that won't really help you if you, as an individual, are being targeted by LE.

I am also WAY out in the open now. I am on Twitter under my real name, and everyone following me knows that I am vantheman666.

For starters: If LE wants to nab anyone here, whether for prostitution or soliciting, the easiest place to do so is in person. Additionally, to bust someone for prostitution or soliciting (and have it stick),  communications alone aren't going to cut it. Unless you're stupid enough to send messages like "does $300 get me FS/BBBJ/DATY/ QWERTY/LGBTQ/XYZ ? With Greek? Preferably a spinner, hopefully underage!!" If you're that stupid then you're a lost cause anyway.  

Anyone running an agency in the current environment should certainly stick to state of the art tech/ privacy measures. Still, that will only protect their clients, and maybe their models, to a degree. If LE sets its eyes on you as an agency owner, they can get you if they want. Merely a matter of time.  

For the smart independent ladies here, and their clients, this simply isn't a concern. I'm not advertising for anything illegal, and my email correspondence is watn and friendly, but never explicit or sexual. I also don't store or save ANY information on my email account, I don't even save email addresses, and delete all emails from a client after our appointment. I save screening info just until after a first meeting (for safety purposes), but I do so on a secure, low key offshore service. Same with any other information a client wants me to save for future meetings or references, like email addresses.  
So someone getting into my email account could find nothing of interest, unless they're constantly monitoring or catch exactly when someone sends an email with any screening info. For that reason, I have a secure screening form on my site, and also offer a discreet, unpublished, secure email address to which a client can send any screening info if they wish.  

As a client, unless your name would jump out to a stranger on a list full of names, you really don't need to worry any more than the average joe about the security of your communications. If your name would stick out, then I would definitely avoid using the services of an agency, since they have much larger targets on their back and a much greater (though still fairly low) chance of having their client lists exposed. If you're actually a celebrity/politician/well known then many ladies will work with you to limit your exposure during screening.  

Obviously if you're going through a divorce or are worried about a spouse, that's a separate issue. Make your passwords and usernames unguessable. Use a password generator/vault if possible. Use a separate device or browser for any escort browsing or communication, etc etc etc. The newbie board hands out advise on this topic regularly. Even for those worried about a nosy suspicious spouse, or soon-to-be-ex wife with a private detective, encryption/tor/state of the art privacy tech is going to be overkill for all but a tiny tiny minority of folks here.