1. I assume the concern about money and cards is just prophylactic and not a real cause for concern for you. In which case just lock you valuables in the safe before you go to bed.
2. Make sure you have clear in your mind what overnight means to you as well as her. Some people think it means mostly a night of passion, others think it means a late evening perhaps with some playtime in the morning. I've seen women on both ends of this spectrum, make sure you know where yours is because it's easy for a misunderstanding in this area to mess up the event
3. Make sure you have in your mind that a woman may need some time to take care of needs both physical and social. She may need to call and make sure her kids got to bed, or to let someone know everything is going ok, or she may need to do some of those things that all humans do. So while you've scheduled her whole evening, if she indicates a need for a little privacy this isn't weird. It shouldn't be overly long, but if she needs 15 minutes you shouldn't be surprised.
4. I like showering in the morning with women. Not all women enjoy this. If you like it, don't assume she will.
5. Make clear when you think the date will begin AND end. Some women do breakfast, others need to get to their job or pick up kids. Some women think an overnight starts at 4 others at 8, it makes a big difference in activities and worth.
6. When planning the expense keep in mind things like room service or mini bar, many times these expenses happen and they can add up quickly, especially if the mini bar includes alcohol.
7. Some men pay for the room with points and secure with a credit card, expecting to have a zero balance, and pay with cash or a gift card if needed when leaving. Some women will use valet when arriving, and if they leave after you finish checking out the valet expense may find it's way onto your card after the fact. If you have a SO who sees your bills this can lead to fun conversations.
8. If you've seen her a few times, but don't already know you might ask about special foods or allergies. Nothing like ordering expensive champagne only to find out shes been sober for 5 years.
9. Depending on the hotel you choose and the trust level you have I sometimes put the women on as guests to the room. This is particularly good if you do a multi night stay. I do this in vegas so if I'm at the tables and she wants to get a sweater she can. But the more important reason is if the neighboring room figures out whats going on (especially if you have 2 or more girls in the room) they sometimes will complain frequently and loudly to security. Some hotel security are empowered to eject any non registered guests, but to kick registered guests has to be bumped to someone much more senior and they generally let it pass instead. In 40 or so overnights it's only happened once, so you may never experience this.
10. I'd recommend and most women will expect some activities outside the room. At least dinner, shows or something like that might also be fun. I like to have some fun, then dinner, maybe a little more fun, then a show, then some fun before bed with a quickie before she leaves in the morning. Consider this when planning, as she will most likely not be expecting 12 hours of continuous sex.
Sorry for the length
Night
Serena x