Hi!Since I know a little about what you've been up to, I'd say you can use points to chase eclipses
(we actually used 60K of our Hilton Surpass bonuses (100K/each) to stay 3 nights for the eclipse).
I'll let the experts chime in on the other stuff, but I think I'm one of the few on here with any Flexperks experience. For us, we are in a Delta hub and our OLD Delta cards w/US Bank became Flexperks cards way back when, so we kind-of accidentally got on board with that. What we like is the flexibility - can be used for any airline. That's also good, as we don't have great Southwest service or other competitive options (Delta dominates MSP for most destinations, it seems). I think you have more decent options, so you may have better ways to fly free. So, we have our old converted Flexperks Visa cards, but got the Flexperks AmEx cards last year when they had a 30K bonus each (enough for $600 airfare each). We did that spend, used a combined 80K points for 2 Icelandair flights to France that were just under $800/each, then cancelled the AmEx cards before the annual fee. One thing a lot of people don't like about Flexperks is that, for instance, if your flight is $399, you can get it for 20K points, but if it's $401, it will be 30K points. There is a hard line there at $400. I probably wouldn't get Flexperks with a bonus of less than the 30K we did. And, for many people, there are better cards. But, for us, they have been useful and we've gotten reasonable value.
Also, regarding the Hyatt, we just did those and got in at the tail end of the offer for 2 free nights. They have since changed it to 40K points. In our case, the rooms we booked were only 15K/night, so it would have been favorable. But, look at where you'd want to book and see if the 40K points will get you what you want (vs. the any hotel free night offer they previously had).
. We originally started playing with cc to just do a Disney trip this year, and that was my only goal. I'm now realizing I could have been dreaming waaaay bigger
. Like Chile 2019!! (My kids are fully bilingual in Spanish, and we'd thought we would do Spain that year, but I'm about as hooked on eclipses now as I am on Disney) I am debating getting the CSR (I have a CSP that I would downgrade to a freedom) and then stopping for two years, mostly bc that SW companion (or just SW points) are SO valuable to us. There is a dedicated terminal at our airport, so we go from parking to the gate in 20 minutes, they go almost everywhere we want to go, and they often run very discounted sales to places we frequent (Disney and Boston) plus the baggage allowance is insane. I am actually at 4/24 now, and could get the CSR UR points to use for other redemptions, but then I'm totally done until late in 2019, at which point we would prob wait until 2020 to start over with SW. I haven't paid for a flight in nearly two years now, so I will need another way to get airfare!!! 
Since you're looking at expanding your horizons, I'm curious if you've thought about combining your SPG and Marriott points for a 7 night certificate and airline miles through their Hotel + Air packages. I've been toying with the idea, but we'd probably never stay in one place for 7 nights in a row, as tempting as the offer may be.
You're right! I was only seriously looking before the merger and was focused on Marriott. SPG seems more restrictive for fewer airline miles, so if the point is to rack up as many SW miles as possible in lieu of the CP, Marriott seems a better choice, no?
My thought with SPG is to do two 5-night stays at the Dolphin during 2017-18. We are buying park tickets with rewards from 2 Barclay Arrival Plus and a Capitol One Venture, then upgrading to AP's. I plan to bookend the Dolphin stays with some sort of cheap AP room rate, to give us two 9-day trips for the cost of four nights at a Value or Mod (or renting DVC for faraway trips.).
Actually I think that was me. No 10x points on my new Freedom, probably because I converted from CSP to Freedom after making the purchase at Walmart.
A few things to remember. Marriott points convert to SPG points and vice versa (instantly). SPG points transfer to airlines, so many consider them more valuable . Since Marriott bought SPG, no one is sure exactly where the rewards programs will go, but Marriott has said the plan is for one program eventually.
Well you could convert Marriott points to SPG points for Swan/Dolphin or look at Marriott outside the park and either use points or pay cash and earn more points. Personally I prefer Dolphin for 10k points/night and converted my 100k Marriott points to 33k Starpoints. But that's where this game is good, cause you can do whatever is more appealing to you. (Fwiw, you might want to consider your goals. Mine is "free vacations" @calypso726 likes to fly first class for her ABD vacations. Both of us like using points for those goalsThis is where my head starts to spin! Would it be better to get two five night stays at Disney (we stay all over the place, but most frequently stay at BC, which I usually pay $300-ish a night for, mostly for location. So for us, I would spend $3,000 or so on hotel stays oop for those nights. I can't get a comparable trip with Marriott points (at Disney)-- can I? And use the Marriott points for something like a Ritz adult-only stay? Help!
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agreed, everyone here is very friendly & helpful. No snarky comments, or ripping on people for their choices (or mistakes).
And we ALL make mistakes at one time or another! They're embarrassing but I like knowing I can ask and discuss with others here when I'm in a jam with something & get help instead of useless flak.
Thank you for saying this. I was lamenting that I got the SPG earlier this month with a 25K bonus and then pulled up a 30K incognito. I wasn't going to bother calling because everything I read said Amex doesn't match. But after seeing your post I decided to give it a shot. I just called, and they asked for a promo number. I had grabbed the T&C when I pulled up the offer, and there was an ID code in there. I gave that to the agent and she's escalating my request for the 5K additional points. It's not a guarantee, but she never gave an indication that it wasn't possible, so we'll see.
Goals: be a professional travelerWell you could convert Marriott points to SPG points for Swan/Dolphin or look at Marriott outside the park and either use points or pay cash and earn more points. Personally I prefer Dolphin for 10k points/night and converted my 100k Marriott points to 33k Starpoints. But that's where this game is good, cause you can do whatever is more appealing to you. (Fwiw, you might want to consider your goals. Mine is "free vacations" @calypso726 likes to fly first class for her ABD vacations. Both of us like using points for those goals
In all seriousness, though, I would say our goals are hotel stays/as much free airfare as possible, not necessarily luxury travel. I spent the last couple hours mapping out a cc strategy for the rest of the year. I think if I open a Hyatt and Hilton (the one with a fee and the 75k bonus) and DH opens a Hilton, we hits that spend, then I open a CSR (I am pretty sure I have 1 more card--need to check opening date for one I opened before this "hobby") in late Nov, pay off our Jan Disney trip to hit spend (7 nights at BC, all reimbursable BC of a conference
) then do nothing more until Jan 2020, I can cover Puerto Rico (spring Break 2018) with only rewards dollars, plus two more Disney trips on our Jan AP's with free stays at the Dolphin, and we will plan to save our vacation dollars for 2019 trips that we pay for in cash. Then I can start all over in 2020. 
Sounds like a great plan. We paid for Disneyland this past March with CSR bonus (when it was 100k) plus the travel credit. I have booked DisneyWorld for March 2018 at Dolphin with SW flights, paid w/points & miles. Paid cash for tickets Also booked flights w/miles for AZ trip to Grand Canyon, hotels outside the park booked with Hilton points.Goals: be a professional traveler
