My thoughts are that he should pay for the room. Not due to any traditional stance or anything like that. For one thing, it will reduce the potential for him to flake. You don't want him to flake, because it can make your wife feel shitty. The more he has "invested" in this, the higher his regard will be for her. If you pay for the room, it's like you're offering him an incentive of sorts, and my feeling is that he should be all-in and highly motivated. Also, it should be a nice place. Maybe not 5 stars, but not the No-tell Motel either. Unless you, or she, is into the idea of it being a cheap hotel of course. Otherwise, the nicer place will enhance her feeling of being desirable, and make her feel more comfortable. One guy my wife had agreed to meet told her her would meet her at one of the rattiest hotels in the area. Purely being a cheapskate and not wanting to invest much in getting his dick wet. Forget it. Actually, I think he had already booked and paid for the room when he told her. She told him to enjoy himself being alone, because she wasn't going to meet him at such a place. She's worth taking to a nice place, and so is your wife.
I once suggested to my wife that she take a guy she was seeing out to dinner on his birthday. He'd been courting her for a while, and she'd decided that she'd give it up to him on his birthday, and asked me how to make it happen. I told her to take him to a nice place for dinner which is next to, or in, a nice hotel. To book a room in the hotel, and go there in advance to stock it with her lingerie, refreshments, candles, music, etc. Then after dinner, to excuse herself and find the waiter, pay for dinner, and arrange to have the waiter hold off for 10-15 minutes or so, then to bring him the folder which normally holds the bill. In the folder, he would find an envelope with a birthday card inside. Along with the card key to the hotel room and the room number, and a romantically worded invitation for him to join her there.
She'd be waiting there for him on the bed in her lingerie, candles lit, music playing, pussy dripping wet with anticipation. The idea makes my dick hard even now. She (wisely, I think, in hindsight) rejected this idea outright. No way was she going to pay for dinner, much less a hotel room. It would make her feel cheap and easy, and like she was chasing after him. YMMV of course....
My wife told me there is no backing up now. She already texted him...
I said its ok, I just want to know when, and that it would be good if she took a few photos. I feel like I shoud book a room for them to meet, it would be my pleasure.
Any thoughts?