Sounds amazing! Fwiw I got upgraded to a balcony room and had early and late checkout with gold status when I stayed on a points certificate last year.
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I’m rolling with new admiration on how you put together such an awesome trip with so little out of pocket expenses! Enjoy!
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That is freaking insane!
I can’t wait to follow the trip!
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You’re my hero.
I do all my other vacations on points so I can spend actual money at Disney. And here you are doing them all.
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When I read posts like this, it makes me think I am doing everything all wrong! You seem to have amazing deals! How do you earn so many points? Tell me your secret! All we have is a Discover card and Chase Disney Visa.
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There’s sure no wrong way to earn points, but there are tactics that are more lucrative. 
To really put together a ton of points you have to play the sign up bonus game by getting new cards and hitting the spend - that will get you many more points per dollar spent than typical points earned.
Cash back cards like Discover etc are nice, but when you earn transferable points like Chase Ultimate Rewards (UR) and Amex Membership Rewards (MR) you can transfer those to partners get multiples of value out of them. For example, using Chase UR to book a Hyatt stay at the Hyatt Regency in Maui was almost 5 cents per point in value - which is a lot better than a 1% or 2% cash back card.
You have to be mindful of the rules at each bank for time between applications, personal vs business cards, Amex’s 1-time bonus per lifetime per card type (AND the ways around that), plus Chase’s 5/24 rule.
(BTW, for biz cards: Many people do not realize just about anyone has a business, even if it is just selling something on FB marketplace or a yard sale. You operated as a sole proprietor, no paperwork to create a business needed.)
There is definitely homework to be done to learn the ins and outs, plus you want to keep track of everything fairly well to maximize things.
The thing people tend to ask about most often is how it affects credit score - the quick answer is it doesn’t really for the long term, and in fact with more open credit your score can go up. After small dips with each new card, we’ve both bounced higher over time and we started out near the top of the FICO scale.
I highly recommend taking the free 10x Travel course - you can go through it a little at a time to get a good base of knowledge on all of this. 10x also has a top cards list that is very useful - most often it is best to just start at the top of that list and work your way down.
The short version of our tactic was two utilize 2-player mode with DW and myself, first picking out cards that are needed to get you started in the game and had high bonuses.
Last year I started with a Chase Sapphire Preferred for 90K Chase Ultimate Rewards.
Once I hit the spend, I used a referral link from my DW’s Amex Gold to add an Amex Platinum for 150K. (With her referral bonus and spend I ended up with something like 190K Amex Membership Rewards.)
Then we worked some Chase Ink Business cards at similarly high bonuses (90K each)…back and forth.
If neither of us had a card that generated a referral link I reached out to people I know from here and the Backside of Magic groups to use their link - If the banks are giving away points I want someone to get them! 
I started a thread awhile back and have been posting more details on various tactics there.
I really started getting serious last year after years of thinking about it because I want to increase my visits down to Miami to see my Mom and sis. Mom’s going to be 96 this year and our taking the kids down every 2 or 3 years is not going to cut it.
My DS19 and I headed down a few months ago:
Our Hyatt Place stay would have cost almost $800, but I used 24K Chase UR.
Our Southwest flights out of our local Islip, NY airport would have cost the two of us about $500 round trip, but in reality cost me 16K SW Rapid Rewards and about $22. (He flew free as my companion.)
My only expenses there were a car rental and food. Plus, with all of my premium cards I had travel insurance on my trip by using the Sapphire Preferred to pay those airline fees, and I have elevated elite status at all the car rental agencies. So, with National I was able to go right to the lot and pick out any car from the Executive Aisle. Some very cool cars to choose from!
This year I’m going to have my DW earn her own Southwest Companion Pass so we both always have them - then every flight is half the points for us!
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OK, This may have been discussed in another thread this year where we were comparing forum editing tactics? But, even if so I’m going to add this here because it’s where I’ve figured out how use it:
Using a table can make posting photos in Discourse (the software that powers this TP forum) better.
It has always annoyed me when I had to just photos all in a row when they would look more better side by side. Well, turns out it is a simple thing to do! There’s just one little hitch I’ll explain later.
To protect the innocent who are not enamored of technical table discussion, I’ve placed the details under this clickety thing. If you are interested - click away.
Click to Show/Hide the Geeky Details
Above in this thread I’m using this trick for the Grand Cypress photos.
To post photos into a table, you have use the | (aka “pipe”) character in between items and the forum will separate everything on each side of the pipes into columns.
Below is what the text looks like for that photo table above as I edit:
So, the first row is the table header column.
“Hyatt Regency Grand Cypress” is the header for the first table column, then the | pipe sets up the next column - If you want the last column do be blank as I did above, be sure to add an extra |pipe at the end of the line. Originally I didn’t realize you could do that so just entered “.” in there because I didn’t need another text column header as these are just photos.
The 2nd row defines the number of columns - this example has two columns, but you can put as many of these side by side as you want. (Although a lot of columns will probably make people have to scroll left and right.)
The next lines are just the content of each row and column - again separated by a | pipe symbol. (See red arrow in pic above.)
The one GOTCHA with photos you upload is the code for them will have a |pipe symbol in them which will confuse Discourse and break the table. The simple fix for this is to “escape” the pipe by adding a \ backslash character before the | pipe.
| Test Table Col1 | Column 2 | Column C | Bazinga |
|---|---|---|---|
| this | is | only | a test |
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What I am deciding now - Park Days.
Our family has never had park hoppers since we didn’t feel it worked well for us when kids were small.
Staying near Crescent Lake with kids now DD16 and DS20 I’m thinking it will be beneficial to have the opportunity to jump into EP at a whim for food etc and take advantage of the late MK & AP nights.
I’m also thinking I like the 3-day park ticket price better than the 4, but also don’t think at all it would be a good idea to remove a day when we have SO MUCH we haven’t seen:
Toy Story Land, Galaxy’s Edge, Tron, GOTG, Remy.
In HS, DD16 has also never gone on Star Tours or RR and none of us have been on ToT.
Can you believe it? Our last two WDW trips were actually more resort-based where we only visited MNSSHP one year and AK the other. In AK, DD stepped up her game and tried Everest - and then we went on multiple times.
So, this year I have a feeling it is going to be…
Assuming we go for the 4 days (we will) - I’m planning on convention tickets, so will also have a free water park day - right now I’m planning for us to use that during the pre-cation stay while at Grand Cypress.
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This is amazing! Thank you so much!
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Well you’re making my trip report look about 64% less nerdy! 
So excited to “read all about it”! That is some amazing work with the points!
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When is this trip again? You’re deciding now about tickets?? 
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Looks like he’s deciding on 4 days between August 13-19th. 
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Yeah I’m like… less than 60 days and no tix?? What about the ADRs? Aaahhhhhhh!
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The problem here is getting my DW to commit to ANY trip. (Edit: This sounds weird, so wanted to add she WANTS to go on trips and we have a great time on them, but will be the first to tell you she has a bad case of decisionitis.) Also, my daughter had a couple of internships outstanding and I didn’t know exact dates.
This trip started out as a trip to Maui booked entirely on points, was awesome deluxe suite at the Hyatt Regency. But someone has no interest in Hawaii, apparently. It is our 25th anniversary this December.
So, I finally just booked a trip I know will go over well and at least upgrading the hotels etc. for us.
I’m not too worried about ADRs, were have so many places we haven’t eaten I’m sure we’ll grab stuff late in the game we’ll enjoy.
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You don’t have to have tickets to do ADRs do you? Just the room, right?
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Don’t even need a room unless you want to book for length of stay.
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You don’t have to have anything to book 60 days out. It’s just so ingrained in me to book everything asap and as far out as possible like we were trained in the before days.
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Amazing planning! In case a small dose of optimism helps for the room category: we booked a no-view room at the Dolphin the week before Christmas, and got a 6th floor with a stunning room of Crescent Lake/Boardwalk bridge and could even see the fireworks above Epcot. We had a Marriot Bonvoy membership (from another recent trip where it got us a cheaper nightly rate), but as far as I know zero points or status. Fingers crossed you’ll get lucky.
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Today’s Meditation: Car Rental
As I mentioned above, our trip is happening in a few steps:
3-nights Grand Cypress pre-cation (Thursday - Sunday)
5-nights Swan
1 night Hyatt Regency MCO
The first leg of the trip will have some serious hang out time in our Grand Cypress Suite, so we’ll likely want to stock up on food stuffs since we have that killer kitchen and dining space.
Plus we want to hit Disney Springs and probably spend some time at Coronado Springs, since Three Bridges is suuuuper-high on everyone’s fav list for dinner.
So, with all of that going on, plus the need for transportation from the airport, I figure it will be to our advantage to rent a car at MCO for those first 3 days.
But: Hoo boy prices.
After some watching, I was able to catch an Avis rental for a full size car for $361.
That rental is for pick up at MCO and drop off on Sunday at the Wyndham in Kissimmee.
I have elite status in each of the rental companies via my travel credit cards. I really like National’s status because if you book a mid-size or above you get to grab any car from the Executive aisle and there can be some pretty nice cars there! My son was psyched to grab a new 4-door Jeep pickup on our Miami trip, but there were Audi SUVs and as we left they drove up some BMWs.
(Pro Tip: I used my Chase Sapphire Preferred (CSP) to book that Miami rental, and that card offers primary rental car insurance. BUT: Half way through the trip I looked something up in the terms and realized that certain cars are excepted - including cars with open pickup beds. I was then a little nervous until I returned the car!)
Anyway: National’s prices were bonkers : $499 for the same rental: full-size car, pick up at MCO and drop at the WDW Car Care center. When I first checked, even if I priced a rental with return back at MCO it was still over $400.
However, today that MCO-return National price was different: $309.
(The Car Care center return option is STILL $499. Pretty nuts to charge $190 for a different return location in such a high volume location.)
My plan on Sunday was to check out of Grand Cypress, drive the family over to the Swan to drop them and luggage off, then return the rental and Uber back.
So, now I’m wondering if it might be worth going with National for the chance to to get a nice car upgrade, but have to deal with the time required to go all the way back and forth to MCO on Sunday.
National will likely end up slightly cheaper even taking into account a longer Uber.
Hmm.
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