Here is the main advantage of established schools vs newer schools for competitive specialties (imo):
I applied/matched into ortho and was the 3rd graduating class of a new school. At the time, my school had no ortho residency or anything. The students from established schools were able to spend a lot of time at their home school's program from MSI-MSIV by shadowing the PD, attending weekly conference, going to ortho events. They were more familiar with the knowledge, residents, how to excel on ortho rotations, knowing what needed to be done, etc.
This is pretty much the only advantage I saw between them and me. To counter-act this you can potentially do this at any school as long as you are aware of it. Start shadowing at a program during your earlier years esp during breaks/vacation; do a 3rd year rotation with that program; do research; be involved when you can; etc.
As for going to a new school...yea they will have problems (as will established schools but at least the newer schools will/should be more flexible in trying to fix them) and not everything will be set up for you. I just kept my head down, did my thing, did well on boards and in classes; no one cared where I went to school on any of my interviews. I chose my school based on location for personal reasons.
Going to a new school made me more pro-active since I was used to not having everything set up for me and just rolling with the punches. PDs like people who are pro-active, people they don't have to spoon-feed or babysit. Even if you go to an established school, it's important to be pro-active, make things happen for you, don't expect anything to be given to you. You can have all of the advantages I mentioned above but if you don't make use of them, they are useless.