Took some thinking, but I think this is where I am at as far as what I will hold and how to spread out the spend. If this helps anyone, great! If anyone sees opportunities/better cards I have overlooked, great! Feel free to comment, thanks :-)

Holding
CSR - $450 ($150-AF after travel credits)
AMEX Platinum - $550 ($50-AF after Saks credit, Airline credit, Uber credit)
Chase Ink Preferred - $95-AF
Chase Southwest Priority - $149 ($74-AF after SW credit)
Chase Southwest Premier Business - $99-AF
Discover - $0-AF
Costco Citi Visa - $0-AF (with COSTCO membership)
Amazon Prime Visa - $0-AF

Spending
ALL GAS - Costco CITI Card 6% Cashback w/executive
ALL COSTCO - Costco Citi Card 4% Cashback w/executive
ALL Dining - CSR - 3 pts/$1
ALL Rental Car - CSR - 3pts/$1 & goes towards travel credit
ALL Cable/Cell Phone - INK PREFERRED - 3pts/$1 AND provides full insurance on ALL phones on plan!
ALL AIRFARE (non reward) - AMEX Platinum - 5pts/$1
Other Grocery Stores: AMEX Blue Cash Every day? 3% cashback
Amazon Prime Visa - $0-AF for 5% at Amazon & Whole Foods

thanks!