Great points and sorry I was so vague. You're right in that everybody's situation and goals are different so answers to the same question will vary from person to person. Anyway, here I go. Hopefully my answers to these questions will help you and others with advice and suggestions for me. Thanks...
- Do you travel?
Yes. About 4-5 times a year, all for pleasure, and almost always domestically. A couple times to visit family so hotels are not required.
If yes, do you have a prefered airline?
I'd love to fly on Jet Blue more often but either it is usually too expensive or doesn't fly into my desired destination. It ends up being mostly American, United and some Delta.
Hotel?
No preferred brand although I am more than fine with being loyal to a brand because I they are a partner of my rewards program and/or I can get better perks there because of my reward program. Not interested in the super budget hotels. Places like Hyatt Place or Marriott Courtyard would be my low end and love to stay at Four Seasons, Ritz, Mandarin, St. Regis if I can make it happen. FYI I'd love to use points towards a cruise if that's possible although I don't feel it is from what I've read about the programs.
- Do you have status already with an airline? Hotel?
Member of most airline FF programs and Hotel loyalty programs but don't have status on any of them. Might be nice though 
- Are you comfortable booking award travel with miles, or are you just looking for a way to convert points into cash toward bookings?
I am comfortable doing both although I don't want a crazy amount of hoops to jump through to book stuff unless the savings is tremendoous. I'm more interested in convenience than saving a few bucks. Needs to be a lot of bucks to get me to put in significant effort and work to book stuff.
- What does your spend look like? Which categories do you tend to spend the most in?
I spend about $1,200 a month on restaurants and groceries, hence the Gold card which is amazing for me. Another $450/month in cell and cable. $400-$500/month on entertainment (movies, concerts, sports). Rent and auto lease eat up a big chunk and then lots of miscellaneous stuff like clothing, pet, insurance, and many other categories that aren't a huge part of my spend.
@Anonymous wrote:Great points and sorry I was so vague. You're right in that everybody's situation and goals are different so answers to the same question will vary from person to person. Anyway, here I go. Hopefully my answers to these questions will help you and others with advice and suggestions for me. Thanks...
- Do you travel?
Yes. About 4-5 times a year, all for pleasure, and almost always domestically. A couple times to visit family so hotels are not required.
If yes, do you have a prefered airline?
I'd love to fly on Jet Blue more often but either it is usually too expensive or doesn't fly into my desired destination. It ends up being mostly American, United and some Delta.
Hotel?
No preferred brand although I am more than fine with being loyal to a brand because I they are a partner of my rewards program and/or I can get better perks there because of my reward program. Not interested in the super budget hotels. Places like Hyatt Place or Marriott Courtyard would be my low end and love to stay at Four Seasons, Ritz, Mandarin, St. Regis if I can make it happen. FYI I'd love to use points towards a cruise if that's possible although I don't feel it is from what I've read about the programs.
- Do you have status already with an airline? Hotel?
Member of most airline FF programs and Hotel loyalty programs but don't have status on any of them. Might be nice though
- Are you comfortable booking award travel with miles, or are you just looking for a way to convert points into cash toward bookings?
I am comfortable doing both although I don't want a crazy amount of hoops to jump through to book stuff unless the savings is tremendoous. I'm more interested in convenience than saving a few bucks. Needs to be a lot of bucks to get me to put in significant effort and work to book stuff.
- What does your spend look like? Which categories do you tend to spend the most in?
I spend about $1,200 a month on restaurants and groceries, hence the Gold card which is amazing for me. Another $450/month in cell and cable. $400-$500/month on entertainment (movies, concerts, sports). Rent and auto lease eat up a big chunk and then lots of miscellaneous stuff like clothing, pet, insurance, and many other categories that aren't a huge part of my spend.
If you focus around JetBlue, it looks like you might fall into the category where both UR and MR are equally easy to move into TrueBlue. Mileage bookings are typically quite easy - the trick is finding the flights with the better redemption values. In your case, I would say this is less of an issue as JetBlue is a domestic* airline which has simpler and generally more open award space at saver levels. Because of this equality, in your case I would say UR and MR are of equal value.
With your spend profile, I'm not seeing a lot of reason in getting into UR just yet. Around half of your spend is optimized on the Gold card (dining/groceries). The big multipliers on UR are travel/dining, of which you have a solid dining option already and you don't spend much on travel. You can put the rest of your spend on Gold as well for 1 MR/dollar, or:
1. You can get the CSP and a FU (and optionally also a Freedom) to earn 1.5 UR/dollar. I think that's a diminishing return for you, though - $95 AF plus two new cards (CSP + FU) to effectively earn an extra 5,000 - 10,000 points over putting that spend on a MR card you're already paying for. You'd break even or come out slightly ahead, but that's up to you if you think that extra value is worth the extra work over just running it all through the Gold. You'd run all non-dining/grocery through the FU, and would pay for the CSP for nothing else than the ability to transfer UR to JetBlue. Not efficient, but not the worst you can do, either.
2. Do the above and ditch the Gold. Your grocery and dining point earning will fall, but you'll shift from a $250 AF to a $95 AF to make up for it. You'd pull in around 30,000 fewer points per year for that $155 savings. This is a clear loser for your profile.
Personally, I don't see a reason to jump in to UR right now. Unless you're looking to churn the CSP for the sign-up bonus (and risk invoking the future ire of Chase), there's just not a lot of upside to going that way right now. Re-assess if your spending or travel profile changes, of course.
* - yes, yes, they fly to the Caribbean and Mexico. These are still basically domestic flights on narrowbody jets that happen to require passports. Transoceanic flights open up a different can of worms because they involve multiple classes of service, vastly different redemption costs based on continent/region, and are considerably more expensive (both in dollars and points), which are the reasons they get carved off into a different category as "international", not because they require passports.
Definitely something to think about. Those UR points are easier to use than MR points I think. Leaning to sticking with one ecosystem for now and seeing how it goes but very possible I follow your suggestion too. Can't everybody just agree and make this easier for me!
I don’t have the Amex gold , but I will substitutite the EDP which i do have in your example. EDP is usually used more for spending , and my chase cards are basically used for 5x categories and sub since there are so many cards and they don’t have life time language like Amex cards have. It’s not that hard to get 200k + ur by just signing up for cards and meeting min spend for the bonuses.
