1. More or less.
2. I book via Marriott. you can call, and there is a swan/dolphin webpage, but it links to Marriott.
3. You link your reservation number via MDE. It is same as if you booked WDW hotels. They don't always show up right away either. It is easy to link a booking.
4. You can book multiple nights if you have enough points. Marriott also allows some combo options (part pay+ part points). I don't know how much he plans to travel, but it takes a fair amount of travel to get 50,000 points. (which I think is current S/D SR points costs? maybe that's just high season points price. Spring break is a high point season at WDW.)
With Marriott, I'm not sure how to explain, but the value of points is VERY variable. Just looking now, two random hotels that are both 25,000pts/night, one would be $131 and the other $149. Sometimes it makes more sense to pay cash over using points. In some cases, it REALLY pays to get AAA. Like the savings on just a short stay more than pays for AAA. Also, AAA stays get generous cancelation terms. Cancelation terms, IMO are very important.
One time when points make a ton of sense is if you want only 1 night at a hotel that has a 2night minimum. It happens during high season at beachfront hotels on weekends. Typically, points are a good option during high seasons and often on weekends. Other times, Marriott offers discounts and deals no the cash price, but the point price is not discounted. Once in a while, there are pointsaver deals = more or less a sale point price. (A lower price when using points).
If you stay 2 nights, but one is on points, and the 2nd is cash, they can link them.
One more time points are a plus is point stays have generous canel policies. Just make sure if you cancel that your points are ACTYALLY returned to your account. Soemtimes they forget.
Another thing is the more points/stays he accrues, then he'll reach a higher status, and then you get extra perks on every stay. Like if a hotel isn't full, the hotel might upgrade his room for free at some hotels.
