Sounds like you should focus on BA Avios (for domestic including Hawaii) and United. So CSP takes care of both of those, but you can get BA Avios faster with several cards:

Chase BA (50K, 1 mile per $1)
Amex Everyday Preferred (15K, 1.5 miles per $1 if you > 30 transactions per cycle)
Amex SPG (30K including transfer bonus, 1.25 miles per $1)
Amex PRG (25K, 1 mile per $1)

For hotels, look into the ones that offer free nights with sign up:
Citi Hilton Reserve (2 weekend nights)
Chase Hyatt (2 nights)

And, of course, as you mentioned, fixed value travel rewards cards such as Arrival are good for plugging in holes where you don't have points or want an independent hotel / accommodation.

I would get the EDP or SPG now and maybe do the BA later in the year if needed to space out your apps.