Well....I'm the OP. After spending the day researching and checking pricing for a handful of future trips with other airlines here is what I have come up with:
1. Keeping the MR points for use with hotels is useless for me. (we are timeshare users)
2. The TP will still get me more flight points vs a simple Marriott to airline transfer.
3. It will be a coin toss if the TP is with SW or JetBlue. SW may win because of their easy change policy.
4. I need my points usage to be in the form of flights.
Whichever I end up - SW or JB, I will supplement what would have been CP with transfer from Chase Ultimate Rewards.
5. I will apply for a SW visa via a referral from my husband and should get 50,000 SW points as a start to building up the SW points needed to get the CP.
First time in about 5 years I'm sitting here without a CP and realize how valuable it really is now that I'm pricing out flights that are running about $900 round trip. (high demand school vacation weeks)