If you can find one with a decent battery health, the 11 is definitely your best bet for a budget friendly, not mini, iPhone. PerfectRec has the iPhone 11 at an 84% match for someone who wants an affordable iPhone that's not small. If size is more important, you might consider a used 12 or 13 PM.

Personally, I'd go for the 14. If you're like the typical american and use your phone for 5 hours a day and keep it for 2.5 years, that $90 price difference works out to about 1.9 cents per-hour.

Is 50% more ram along with the other late-model improvements worth that to you?

I might think about it in terms of cost per hour of use. The typical american keeps a phone for about 2.5 years and uses it for about 5 hours per day. If you last bought a phone in 2017, it sounds like you keep your handsets for about 2x as long as the typical person, so let's say ~9,000 hours of screen time. That would put the base sized 14 Pro Max at about 12 cents per hour of use. The 14 Plus, on the other hand, would be about 10 cents an hour of use.

So the question is, are the other Pro Max features like a better camera worth 2 cents per hour to you? Based only on size and battery life preferences, PerfectRec has the 14 ProMax at a 59% match and the 14 Plus at a 52% match for you (results), which is pretty close. If you can still find a 13 PM at a local retailer, that might be a happy medium. But the big picture is that if you're getting a ton of life expectancy out of your phones, the incremental cost between the Plus and PM isn't that much.

Personally, I'd go with the 14 for the battery life, but I think it really depends on if you want to prioritize. With the smaller phones, you have a very stark tradeoff between size vs camera and battery.

If you're No. 1 priority is a small size and you have no opinion on anything else, PerfectRec has the 13 Mini at a 41% confidence match for you. But that would change dramatically if you care about camera or battery. If you say battery is more important than size, it has the 14 Pro at a 53% match for you. That number would creep up depending on your camera and budget priorities.