I would say if you have the resources, maybe 4 cycles (like I did) is enough. If you get past 4, consider other options. Which aren't as bad on you mentally, physically, emotionally. Like PA or NP. In the all encompassing ball of providing medical care, those are fine.
That said, why 4 tries. Because there are things beyond matriculating that are foreboding based on a "sampling" of the pre-med road. Basically the MCAT. In relation to NBME/USMLE licensing. Or even COMLEX/AOA. As Law2Doc mentions.
I mean, there are many instances where your MCAT score doesn't correlate to your Step/Comlex score, but those instances take realistic honesty. I mean, if you got a 24 on it because your dog died, as you got dumped by your SO, while you get evicted all the day before - give it another go and try your damnedest, and hopefully retake in a non-similar situation. However, if you've taken it 3x and you are +/- 2 pts and still averaging a 26, it's rare that you'll have some magical part of your brain unlock and you bang out a 36 the next attempt.
Step 1 is BRUTAL!!!! The MCAT is a trickle compared to the deluge of Step 1 (like I tried to relay in some other thread and got told I was crazy by some PRE-MED). And as was pointed out before, >1 attempt on the Step is frowned upon. There are FMG's who are passing it on their 1st try. And just passing isn't much either. Your 200 on it will get beat by some FMG's 230 for the same residency spot (w/o debating the AMG v. FMG thing). And UNLIKE the MCAT, once you pass the Steps, it's not like you can retake it. That 200 is an indelible mark on your residency app.
And medicine is NOT like it was 10 years ago. Any doc will tell you. The residents/attendings and even us MS3/4's who chime in will tell you that. I have my own personal reasons for NOT pursuing being a mid-level. And I know if those reasons, were to diminish, I'd be asking MS3-self, WHY did I just not become a NP or PA!?
I spend 12-14 hrs/day in the hospital for IM. And weekends off are referred to as "golden weekends" because it is rare to get an entire weekend off. I am NOT even an intern! And when I think about how IM is what I want to do w/ my life, if it weren't for my personal reasons for being in med school, and waking up every single day...there's NO WAY I could look in the mirror and tell myself, "No worries, after you graduate from med school, you have to do this for 3 more years if you just want to be an internist."
There's a lot of humanistic crap out there these days. YES, ok. The Secret will get you whatever goal you want. Be damned if anything or anyone get in your way. You can do whatever you so choose. But base stuff in some realism. My dream board has me playing in the NBA as a 5'8" Filipino and making several children w/ Nicole Scherzinger. Hasn't happened.
Am I NOT driven enough?? And I'm being serious. Am I just a quitter? I don't think so. I'm just realistic.
W/ that said, 3 maybe 4 tries. Every subsequent try, really begin to consider something else. If medicine is your thing, all else be damned, at least start considering PA or NP. I'm sure there's a few people who have responded to this thread who are daydreaming right now about how they wish they went mid-level.
(P.S. - Shjanzey you at least have the correct attitude. If you can't wait to wallow in the "mud" of medicine even after a long day, that is something to work on relaying during interviews)