Since I think its more helpful to have a hard-evidence based response than an opinion based response from based on what we all know is most often true of the medical school system in the US (that mainland schools are much better than foreign/off-shore schools), here goes.
Sackler is actually a great school. Their alumni are spread across the US in teaching positions. In fact, I interviewed with an OB/GYN that is also a professor at University of Chicago. They have people all over, from UCLA, USC to practically everywhere in the East Coast, including some of the main hospitals out there - Johns Hopkins, Beth Israel Deaconness, Yale/New Haven...don to Emory...check out the website.
It is affiliated with the state of new york, and statistics are that 90%+ get first or second choice residencies. A portion of clerkships are done in the US to get the necessary recommendations, and most often I have heard physicians say the students they have worked with from Sackler are much better prepared for the practical/hands on work and are much less shy performers, but the paperwork side is what lags.
Finally, I've checked out all of the match lists for the past few years, and am looking at the 2008 list right now...It includes pediatrics positions at Johns Hopkins, a Neurosurgery residency at Brown (Rhode Island), Neurology, Oncology, Pathology, Radiology, Dermatology, Orthopedics...pretty much anything you could imagine is involved on the list.
I also recently spoke to an emergency room doctor at UW-Health in Madison, one of the largest hospitals and most well-equipped trauma centers in the state. He told me his path involved mostly public schooling. He went to a "lesser known" medical school, and still ended up with an MD. His residency placed him with other match-ees from Harvard, Yale, Cornell, Johns Hopkins...In the end, hard work is what takes you to the next step.
After all of this, I am of the opinion that wherever you go, you should go for the experience, not for the name or the prestige. No single school will give you a better chance if you end up being unhappy. If going to Sackler will make you a more calm, relaxed, happy medical student, then by all means, GO! If you would rather go to Duke or University of Washington because they rank among the top tier of Medical Schools within the US Mainland, but wind up feeling a bit out of place, you will not hit pique performance.
Choosing where to attend medical school for four years is incredibly important. Don't base the choice on which place will give you the best opportunities later, base the decision on where you will feel and do your best. If both coincide, then congratulations!
I attended an interview at McGill in Montreal, which is an incredible school. I met quite a few of the students there and while I feel that school is absolutely fantastic, I dont want to relive high school and college. I attended schools with great teachers that taught me quite a bit, but I did not feel like I was in the right environment, and even now I feel as if I performed less than my best. Some of the students I met couldnt talk about anything but the school and their studies. When I spoke to people from Sackler, they spoke incredibly highly of all of the other students there, and only mentioned how happy they are.
So like I said, certain people will do well at certain places. You have to decide you are a
X person who will do well at X school.
Good luck with the decision.