I'm traveling ORD --> CLE. Currently, it's weekly. Soon to be every other week(Sept.) I stay at Marriott 4 days / week.

I am signed-up with Marriott Rewards (~20,500pts)
Recently attained Marriott Plat. Elite
Currently earning Marriot pts over UAL FF miles for my hotel stays
I have an United MP acct. (~112k miles)
I have a United Plat CC(3miles/$1)
I have 21 segments (should be P2 by mid August)
I rent cars once every 3-4 weeks for 4 days, but have to go w/ agency which doesn't give FF miles (Enterprise)
No, Midway is not a feasible airport option for me

Currently using Chase Freedom b/c of recent promo for 4 bonus pts up to $1500 spent on hotel/car/air(only using for hotel/car until $1500) Then back to United Plat for hotel/car

I recently(4-5 weeks ago) signed-up for Chase Continental to get 30k before the UAL takes over (already got the 25k UAL MP years back and say it's a "once in a lifetime" deal...and not able to get more FF miles from Chase CC offer

I have 5 Chase CCs, so not sure I'll qualify for Marriott Chase though wouldn't mind the 30k "free" points and free night stay. Since they said I already had too many cards (but still approved me) for the Chase Continental

Objectives:
1. Obtain most miles/points/etc humanly possible (or FT-ly possible )
2. Intend to use points/miles for travel(most probably International) at some point
3. Aspiring points/miles-whore going crazy over all the 2 and 3-letter abbrev.



Questions:
1. Is it best to go ahead and get the Marriott card to use for hotel points? or continue to use UAL Plat for FF miles? As above, using Chase Freedom for the quick $75 cash-o-la (Is that wise? or mid-guided?)

2. Is it worth my while to get an Amex SPG? (Yea, I just missed the latest killer deal (( )
2a. B/c I travel during the week, I hesitate to get SPG for the dollar-coin deal...simply b/c the UPS station is a frickin' haul to get to and would really eat into my limited time at home to make the pick-up each couple weeks.

3. Am I using the right CCs for the right purposes?

4. Am I right to have switched to being a pts earning at Marriott? The 10pts/$1 even if I switched them over to UAL FF miles, worked out better than the 2 miles/$1 Marriott gives if I choose miles over pts earning...and if I get Marriott CC, then it'd essentially be 15pts/$1. The pts-to-UAL miles conversion even w/o the Marriott CC is better than getting straight miles. (https://www.marriott.com/rewards/usepoints/moreairmi.mi)


Appreciate your insights or things I am over-looking.