re: Opening new personal credit card for rewards purposes. Which one’s right for me?

You would transfer points from your various Chase cards to your Preferred/Reserve. Those are the cards that allow transfers to travel partners. For the business card, you would need to look at the three Ink cards that allow transfers and see which one compliments your spending the best. Getting all three is also an option and they typically have pretty nice sign up bonuses. Once the points are with your Preferred/Reserve, you would transfer them to your Hyatt account and make a points booking. If I can’t get more then $0.02/pt, I pay the cash rate.

If you value breakfast, I would recommend looking into the Hyatt business card too so you can spend your way to Globalist status. For every $10k you spend, you get 5 qualifying nights. Once you get 60 QNs through stays at Hyatt and credit card spend, you get Globalists. You can also get the personal Hyatt card which gets you 5 QNs every year plus a free category 4 night for only $95. My family of 6 has gotten free breakfast including gratuities, which has been as much as $150/day, every time we stay at one of the nicer Hyatts. This includes the Regency. On top of that, you get free upgrades frequently along with other awards as you make your way to sixty nights.

If you like Hilton, look into the AMEX Hilton Aspire. You get 3x points for all spending on that card. Both my wife and I have this card even though the annual fee is $550 year. It comes with a free night certificate that can be used at just about any Hilton worldwide if they have a standard points room available. The certificate alone could be worth $1,000+. On top of that, you get a biannual $200 resort credit, and a quarterly $50 flight credit, as well as Hilton diamond status, and some other stuff. We spent two nights in Key West Easter weekend and each used a FNC. The room would have been about $850 a night and we split our room charges at the end on the two cards and each got credited back $200 of our room charges. $2,100 in value with $1,100 in annual fees and that’s only taking advantage of a portion of the card’s benefits. You can also get additional FNCs with spend on this card. One thing with Hilton points though as that they are best saved for trips of 5+ nights. This is because when you book 4 nights on points, you get a fifth night free.