My "history" was 6, 7+, 8+ (as I initially was very unhappy with the direction of the X), but jumped to the Max. Apart from a possible problem with a yellow hue on my screen (check other threads, I can live with it but the 8+ was noticeably more accurate - or blue!) and a tad less battery life than the 8+ (that thing was the best!), I'm very happy.
All the points I was worried about cleared up in the first day of use. I LOVED Touch ID and was extremely annoyed to see it go on the iPhones. The reason for upgrading from 7+ to 8+ was to get the latest classic style iPhone with a home button and Touch ID and ride with it until I became happy with the new generation of iPhones. Yet Face ID is just so much more seamless and much easier than Touch ID. I don't think about the process of entering passwords or unlocking my phone or authenticating for Apple Pay. It really just "works" (and even with sunglasses!). Touch ID was annoying when your sweaty fingers would cause it not to recognise you and then you'd have to manually enter the passcode or passwords. Only when in the car (it's in a fixed holder) and when flat on the table does it becoming annoying, that you have to get your face into the sight of the IR camera. But other than that: Face ID wins for me (and that's coming from someone who hated the thought of it last year).
I was also thinking about going to the regular XS and the Max seemed a little too large in store. Got it home and I can just say: It felt smaller than the 8+ did! Very weird feeling, as when I then went back to the 8+ to check I realised that the screen felt cramped and tiny! Weird how perceptions can change in seconds!
If you have been on the iPhone pluses in the last years, get the Max. It'll be the only one that makes you happy! And when you watch videos or type, the keyboard will be in the same place / screen will display at the same size as the 7/8+ phones did.
Only software niggle: Control centre is in a damn stupid place and can realistically be reached only via reachability (which I have activated and makes the phone useable with one hand) or it's easier to just reach out with your second hand. But put up with that and you're rewarded with the plus phone we all really want(ed)!