I've begun leaving a few bucks of added cash when we meet at hotels...  specifically to tip housekeeping.  I believe it's vital to keep housekeeping happy as they likely have a very good idea of what goes on in a room...    
I've inquired of my Favs about the housekeeper's tip...  and want to kick in my share.  If she has more than my appointment (I just have to guess) I drop $2-3 on the TV.  If she got the room just for our meeting, $5.  I think my thoughfulness for the staff also reflects on my attitude towards her...  which is always rewarded.  
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what goes on. Unless the lady walks around the hotel clad in hollywood movie stereotypical hooker wear or there is a deli style counter on her hotel door with 15 guys waiting in line, I think this is one of the biggest myths in the biz. The ladies I see, one would have no clue they are in he biz. They dress down when they check in, when I do outcall and request an outfit, they bring it and change into it. Thousands of people are coming and going in a hotel, and I dress well and the ladies I see dress well and blend in well. Older men with younger women is not unusual at all. They could be father/daughters or boyfriend/girlfriend or brother /sister for all house staff knows or gives a rats ass about. I just think its paranoia to think there is a maid around every corner just waiting to dime us out. And how does that play out any way? Does the maid go to the hotel manager and say "I think there is a hooker in room 412 sir." Then he says "Oh great job Debbie! I'll get right on the red phone and the coppers will be here in no time!" We should tip the maids because its the right thing to do. But to thing this will keep us all out of the paddy wagon...I dont think so.

Hotel employees are aware that sometimes p4p sex is going on. Some couldn't care less and don't pay much attention. Others are curious, and are probably suspicious of every single woman who checks in. None of them run to management to report "suspicious activity" unless they are 1) extra nosey pricks or 2) ordered to by management for some reason.

Exactly. Tipping the maids too much can in fact RAISE suspicion. I tip them at the end of my stay, and leave it in the room. I do not ever call them for shit to be honest. I bring my own towels, sheets, and anything else I might have need of, so I don't have to bother them. I also leave my DND sign up whenever I am not in the room, so they don't come in. I agree with you...some people are way too paranoid when using hotels.

It probably varies with the discretion of the hostess and how she chooses to interact with the staff.  On a recent visit, I noticed a huge pile of fresh, nicely folded hotel bath towels and linen on the bureau.  I'm thinking that this is good for me!  Fresh towels!  When I went to the bathroom, there was ANOTHER huge pile of clean towels on the rack.  My hostess is sure the staff have a clue about what she's doing but they never cause any problems for her or her guests ... and, when she checks out, she tips them accordingly.

about her activities & that he didn't care.  She was taken aback but didn't give him any information.  
I agree to keeping housekeeping out of occupied rooms.  My last family vaca, we found housekeeping, swapped towels & told her to leave the beds alone for the duration...  which the hk was happy to do as they have to do many rooms in few minutes.  Yes, the housekeeping tip is left in the room on checkout.  That's a good point, if your hostess has other clients after you, the hk tip might be confusing if left out.  

I spend a lot of time in hotels and I know quite a few management types in the hospitality industry. Escorts using the property to work out of is not a topic that comes up too often and that's mostly because it's not something that they really care about.  Hotels are in business to rent rooms. Period.  It's almost impossible for a hotel to be found at fault for any wrong-doing if an escort gets caught working out of a particular property so for the most part the "don't ask, don't tell" rule is in effect.  As long as the lady doesn't do anything to draw attention to herself she really has nothing to worry about.  I know some girls who think that extra tipping will assure that they are left alone but I also know some who will never tip extra as they feel it draws attention to themselves.  To each his own but, unless you are seeing guys on the half hour and hanging in the same property for three or four days at a time, you really have nothing to worry about.

If I go to a lady's out call I don't feel the need to subsidize her business expenses over and above what I am paying her for her time.  I may tip on occasion and, just like the rest of the donation, she is welcome to use it for whatever she wants.

Tipping hotel staff in my opinion always keeps them on your side and happy to accomodate your needs. Especially if your staying for more than one day at a hotel, it's very important to grease housekeepings palm so they don't mind bringing extra towels, taking all the old ones, and straightening things up Not to mention keeping HUSH HUSH

It doesn't matter what she checks in looking like or how she carries herself, if there's extra traffic, housekeepers are going to notice. I know because I used to work for a cleaning company and every once in a while the ladies would talk about it. They're not scoping out the halls, and she'd have to be pretty high volume, but people aren't stupid either.