This is a copy of the email I sent out to several friends who were getting married and had asked what credit cards my wife and I had opened. Details of the offers and benefits are only as up-to-date as the date of this post.

Hi friends,

Going to try to make this as brief as possible. What credit cards you sign-up for depends on what you spend your money on and how much you enjoy playing the 'points' game e.g. keeping track of what charges you put on which card, how to transfer points to get good deals, etc.

The really short version is that in my opinion Chase overall has the best point system in my opinion, but Amex lets you travel in style. If you spend your money primarily on food and travel and vacation at least a couple of times a year, get the Chase Sapphire Preferred, then the Chase Freedom Unlimited, then the Amex Platinum. I personally really like playing the game, so I have a few more cards beyond that.

For our wedding and honeymoon, we put every expense we could on a credit card (unless there was an extra fee to do so). In total, we opened the Amex Platinum, Amex Gold, Amex Blue Cash Preferred, and Bilt Mastercard. We use points for just about all of our vacations.

Before signing up for the card, make sure to maximize your sign-up bonus. Skip to the bottom for details.

If you want the long version of the credit cards

Here's my basic setup:

I essentially do a variant of the "Chase Trifecta" which are these the cards: the basic no-fee card Chase Freedom Unlimited + the travel card Chase Sapphire + Chase Ink business card. Chase cards are handy because you can transfer your points between your Chase cards (except for the Amazon Chase card, which uses its own Amazon points)

Chase Sapphire Reserve vs Preferred - We use this card for travel (e.g. car rental, plans, hotels, tolls, rideshare, etc) and dining (restaurants, fast food, delivery, etc).
(almost) Everything Else: We use this card for almost everything else. Chase Freedom Unlimited gives me 1.5% on everything which converts to Chase Sapphire points, which then can be used for travel by transferring to airlines or hotels.

The third leg of the trifecta is the business card, which I closed since I recently do not have business costs, but I plan reopen one later this year now that once I switch to 1099.

The next card I got was mainly for the perks:

Amex Platinum: This is the first card we got when we knew we were going to have big upfront costs for the wedding (I already had the Chase cards). It has a hefty fee ($695 per year) that becomes negligible if your expenditures already include the reimbursed categories below. Only really gain points via flights (5x), but that’s also not why I keep the card.

$200 Hotel Credit - if booked through their Hotel Collection and Fine Hotels & Resorts via the Amex Travel portal. We stay at a hotel for some reason at least once a year anyways, so this cancels out $200 of the yearly fee. You can find some regular hotels on these lists too, but when you book it this way you often also get free perks (free upgrades, $100 for hotel expenditures, free breakfast, etc)
$240 on Digital Entertainment - You get reimbursed $20 per month on Audible, Disney Plus, Espn, Hulu, New York Times, and a few more. We pay more than that already for these, so get that money back too.
$200 Airline Fee credit - I usually get the wifi package on flights. You get up to $200 reimbursed for extra airline costs. The only catch is that you can only do it with one airline (you can change the airline once per year) so you have to choose wisely.
$200 Uber Cash - You get $15 Uber Cash per month (and $20 in December). I use it for ordering food mainly; we always spend more than that each month on delivery. Yay, more money back.
Global Entry and $189 dollars towards Clear - we already had Global Entry but I paid my parent's and relatives' Global Entry using this. I was able to reimburse multiple since they are authorized users on the account.
Main reasons I got this card was to make travel smoother

You get access to Amex Centurion Lounges, Delta Sky Club (when flying Delta), Plaza Premium lounges, and Priority Pass lounges. I have not paid for food in an airport in ages. And I love a cocktail pre-flight. The other premier travel cards give you only Priority Pass which usually are not that great. or readily available, especially domestically.
Free Upgrade to Marriott Bonvoy Gold Elite, Hilton Honors Gold, Avis Preferred, Hertz Gold Plus, and National Car Rental Emerald Club. The car rental status upgrade is nice because with Avis Preferred I do not have to wait in line or talk to anyone. I just get into the car and drive away.
Trip Delay / Cancellation / Interruption Insurance - I usually use my Chase Sapphire for this because the coverage is a little better, but if you do not have travel insurance already, this is a nice perk. Gives you peace of mind if you actually do have to cancel last minute for an emergency. I have had to use Chase’s travel insurance once, and it wasn't too annoying of a process. Just remember to put the charge on the card from which you want the trip insurance.

Perks I do not use - $100 on Saks Fifth Avenue per year, free Walmart+ (free shipping and same-day delivery, kind of like Amazon Prime for Walmart), $300 Equinox credit (covers a little over half the digital membership)

Most of those perks are to get my yearly fee back, the rest just lets me travel with ease.

Chase Sapphire Reserve or Preferred?

So there are two Chase Sapphire cards.

Short answer, unless you spend more than $10,333 specifically on travel every year, just get the Preferred. Yes, I did the math.

The main difference between the two cards is that if you are converting points into cash or buying flights directly on the Chase Portal (both of which would be a poor use of your points; you get more bang for your buck by transferring to airline and hotel partners), Chase Preferred points convert to 1.25 cents per point and Chase Reserve points convert to 1.5 cents per point. I still have the Chase Reserve because I got it when the yearly fee was considerably less, but I plan to downgrade. Both of these cards transfer to airline and hotel partners at the same rate.

The math for the Preferred card, if ignoring all other perks aside from points earned through travel (2x points) & dining (3x points) AND if you converted your points directly into cash:

If all you used this card for was dining, your $95 yearly fee would breakeven after spending $2533
If all you used this card for was travel, your $95 yearly fee would breakeven after spending $3800
Since you'd be using the card for both, depending on how much you spend on travel vs dining, your breakeven point is somewhere between $2533 - $3800. I spend that much on food and travel in a month. Maybe two.

The math for the Reserve card, if ignoring all other perks aside from points earned through travel (2x points) & dining (3x points) AND if you converted your points into cash:

Your $250 yearly fee has a breakeven point at $5556

Realistically your breakeven point is lower than either of those values with all the other additional perks. Here's the full comparison table, but pretty much just get the Preferred.

Other cards I have or will have:

Chase Business Card - Get the Chase Business too if you ever end up as a 1099 employee (or have significant business expenses in general). More points to funnel to your Chase Sapphire.

Bilt Mastercard - This card honestly has been awesome. I put my rent on this. It comes with an "account number" and "routing number" so you can use it like a bank account, but it earns 1x points on Rent. So why not? I also got a super nice sign-up bonus with it as well. The sign-up bonuses are not public, but if you open a Bilt Account (before opening the Mastercard) you may get a sign-up offer in your email. I got a 50k point sign-up bonus once I opened the actual card.

Amex Gold - We still had more wedding costs so we figured we might as well exploit the sign-up bonuses. This is their second-highest card (platinum being the top). 4x points on restaurants, 4x on groceries. If you sign-up for this card through Resy, you get another $250 one-time bonus off restaurants. Also $120 off Grubhub / Seamless ($10 per month) and another $120 off Uber Cash (similar to the Platinum card). Not a bad card, although we will likely be ditching it before the year is up. Not worth the yearly fee to keep for more than a year. We got this one mainly because of the nice sign-on bonus.

Amex Blue Cash Preferred - It was zero fee for the first year ($95 per year after that) and gave us $300 sign-on bonus, 6% on groceries and streaming services. 3% on gas. It covers pretty much all the streaming services. The platinum only covered a few. We put HBO Max, Netflix, and Spotify on this card. The 6% on groceries is nice. Likely will also cancel this one after a year. Not sure it's worth the yearly cost. Though I'd cancel the Amex Gold before I canceled this. Essentially if you spent more than $1583 on groceries + eligible stream services annually, you've already covered your yearly fee. Assuming you would have put your groceries on a credit card anyways, then as long as you spend more than ~$2100 on groceries and streaming services a year, then it's worth it.

Amazon Prime - No annual fee, but you can only get the 5% card if you pay for Amazon prime. 5% back on Amazon purchases and Whole Food. $100 Amazon gift card sign-on bonus

Caveats

If you're buying a house / car / anything that requires good credit, remember that opening multiple credit cards will drop your score slightly. If you're on the cusp of credit scores (700s, or 760s) and about to buy a house, it may be a smarter decision to close on the house first. My score took about 6 months to fully bounce back
You have to like keeping track of these things the more cards you have. But from day to day it's actually pretty simple. The only cards I actually keep on my person are my Chase Preferred (for eating out), Chase Unlimited (for everything else aside from groceries) and Amex Platinum (you need it to get into the lounges). Everything else I put in my Apple Wallet and leave the physical cards at home.

How to Maximize Your Sign-on Bonus

Check your personalized offers using the Card Match Tool . Usually higher than what is public to everyone

Highest signup I've ever seen for Amex is 150k (low end around 60k);
Highest for Chase I’ve seen is around 100k (low end around 50k)

If the bonuses currently are average, you can consider waiting. They go up and down throughout the year.
Unless you plan on getting two separate cards (which potentially is a valid strategy if you want extra bonuses) check to see who has the bigger sign-up bonus, you or your partner. Depends on credit score.
Compare that offer against signing up through Resy https://resy.com/amex-offers; their offers come with extra perks that are pretty legit.
Compare that to what you'd get via my referral links. Don't worry about it if your best deal isn't through a referral link, I just happen to get a nice bonus if you sign up through the links below.

How to Maximize Using Your Points

That's a whole different email. But you can always use this calculator to check. You got the most out of your points by transferring to airline partners especially for international or long-haul flights. Point.me is a great tool for finding flights via points (I just pay $1 for a month each time I need it using promo codes easily found on the internet). Also, you can get great deals by transferring to Hyatt if you're just looking for a weekend away. We just stayed at an $800 per night all-inclusive for 20k points per night in Cancun. I keep a spreadsheet with the various transfer partners like the below.

You get less value out of your points by changing your points directly into cash or booking flights via the travel portals. But if you're strapped for cash, it's not a bad option!

That's all folks,

Tim