I have an AP and TiW ....... one bill, one payment. We exchange cash later and like PP said you can shift money on your phones with Apple Pay, Paypal, Venmo, Square Cash ... I do all the time with my kids when they pay bills.
I looked on the website and did see this ....... which I was surprised by number of guests ....
"Unless otherwise stated, discount excludes alcoholic beverages, applicable tax and gratuity, and is valid for the Passholder and up to three (3) Guests. Dining hours vary by location; inquire at time of booking. Locations and operating hours subject to change without notice...... A valid annual pass card and government-issued photo ID must be presented at time of purchase to receive discount."
And again in the Passholder Booklet ..
"Reservations for Table-Service dining may be made by visiting MYDISNEYEXPERIENCE.COM or by calling 407-WDW-PASS (939-7277). Unless otherwise stated, discount excludes alcoholic beverages, applicable tax and gratuity, and is valid for the Passholder and up to three (3) Guests. Dining hours vary by location; inquire at time of booking. Locations and operating hours subject to change without notice."
Have you considered the TiW since there are 8 adults (includes alcohol if you order), since you will have auto-gratuity anyway and it covers up to 10 people? You said you were going to expensive restaurants so depending on how many and how you usually eat on your other AP trips, it could be worthwhile.