Sorry, no special insights from me. There isn’t anything fancy, just do the math on the various deals. Just know that they often hid significant fees and taxes in their advertised rates. The majors are starting to offer the same deals to new and existing customers. No reason to pay cash for a phone if you are sticking with one of the big three. And they usually give you a decent value on your trade in.

But you could switch to one of the minors like Cricket or Metro. They all buy time for the major networks, so service is usually comparable.

TMobile had an IPhone 12 deal for mother's day - maybe wait for father's day

For phone deals check Slickdeals.net - search there for any current deals and you can also set up searches so that when any IPhone deals are posted, you get an email

1st of all, your vaccine shot already comes with 5G so no need to look for that feature.

2nd of all, the family bundle discounts pops up once in awhile with the major carriers. I think Verizon just had one recently where you get a couple of free phones if you switch over? If you're patient wait for those to pop up or else as another poster noted check out smaller carriers like Metro or Cricket.

Are you able to switch plans? If you switch carriers you can typically get free phones.

I switch carriers around once every 4 years.

If you are going to be buying three top end phones that around 3g. Which works out to around 80$ a month spread out over 3 years.

As a note you still typically have to pay sales tax when getting new phones.

An issue is that most carriers have the best deals for 4 phone lines....

Costco.

Just upgraded my husband and my phones and added a line for kid #1 on Verizon. They are running a BOGO free iPhone 12 deal if you switch to unlimited talk and data ($45/each per line) if you don’t already have it. Unfortunately we live in BFNowhere and they don’t offer that deal here right now. So we got a new line for the kid, got a free iPhone SE (deal with the new line), husband gets the free SE and I sprung for a 12 Pro Max. Kid is getting my old 6s+. Really wanted the BOGO deal on the iPhone 12’s but they couldn’t give it to us.

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Harry: "I expected the Rocky Mountains to be a little rockier than this."
Loyd: "I was thinking the same thing. That John Denver's full of shit, man."

Agree with Jim. Either buy it from Costco with better return window (90 days?) or look to switch carriers. I've been with TMobile forever. I just buy the previous years model when Samsung comes out with an update. Although, I'm still using my S9+, on year 3.