No reason not to go for a couple of Hilton cards. The no fee card, the business card. There are 3 personal Hilton credit cards and one business card. It's more than enough to get you all the points you need. The breakfast benefit normally applies to the card holder and a guest. The $250 credit can be doubled dipped since it is card anniversary year if you are more than a year out from your trip. If you got the card now, your card anniversary would be September. You could make a pre-payment on your reservation for "accounting purposes" pay for one night as long as it is not the advance booking rate and get the credit. Then next September your credit would be available again and can be used to pay for another night or possibly park tickets. The free weekend night would post about 8 weeks after you get the card so you could book a Friday, Saturday or Sunday night.
I'm booking for a Northern Ireland and Ireland trip next year. I have secured 4 nights at Ashford Castle in Ireland but I don't have anything booked for our first few days in Northern Ireland because one of the hotel I'm looking hasn't released any point bookings yet. The other isn't one I can book with points but hasn't released availability to book yet. Looking at the Hilton website it appears that they have only released availability through the end of August. There are no Hilton properties of any variety/brand with availability in the month of September within a 50 mile radius of Tokyo Bay. So I'm guessing they have not released the dates to book yet.
Anyhow, my view point of course will be biased because I have the card and I am actively working on getting a second one of the same card and so is DH so we will have 4 between us. Thanks to this card we stayed in over-water bungalows on points in the Maldives which were over $1200 per night and were able to use the Diamond benefit to save a lot on food because it included breakfast and happy hour. The resort credit allowed us to pay for the absurdly ridiculously priced flights to get to the island. Those prices now seen reasonable compared to the yacht ride that
@*WDW*Groupie* will be taking for her transportation to the WA in the Maldives which is also in my future plans.