Well practically speaking, I have to graduate in 6 years or be out so if I had to take another I just won't be returning at all.
But I'm assuming you mean how will PDs view the fact I had to take two "time-outs" and won't need another one when things get tough during residency. Without disclosing too much, both were separate issues that required more than 4 weeks and have been completely resolved. I didn't need much more than 4 weeks (but I did need at least that much) to deal with the problems. For the second leave, I was hospitalized and definitely wanted to return (it really really sucks basically wasting a year of your life and destroying your career at the same time) but I was not cleared by my doctor in time so I really didn't have a choice there. I'm hoping showing that if I can do well and really excel during more stressful times, e.g. board study, clinical rotations I can show that this was just a case of unfortunate circumstances that not only made me a stronger person but won't happen again.
I'm also hoping that since the first leave of absence was after the first semester of medical school (and I was gone for the second semester and then returned) it won't be as big of a deal than say an extended leave of absence during clinical rotations. But there is a voice in the back of my head that keeps saying "It won't matter how well you do now anyways..." and so I was hoping to get more feedback here before I make a decision. Since investing 3 years of my life and a whole lot of money is on the line, some real talk is appreciated.