$37,500 for a 2015 trail with 19k miles on it? That sounds a bit steep to me. You could probably get a brand new trail for about that price.
I thought you were originally going to get a used SR5 or Limited?
As I said, you can get a SR5 10-12 for about $24k, maybe even less.
The Limited's from that time will be a bit more.
If you really want the trail edition, expect to pay $29k-$31k, at least, for a mildly used one.
The key for all of the above is finding a 4runner from 10-13 model years. The newer ones (14-15) will cost more, even used, due to the exterior face lift, even though the inner mechanical parts didn't really change much.
This is totally a subjective issue, but IMO I don't see a point in paying for these SUV's at their brand new MSRP's. Yes they are Toyotas and yes they are reliable. But after 2-3 years of ownership, you'll see about 25% depreciation. I say let someone else buy the car new and suck up that loss, while you be the one who buys it off them for a nice discount. This requires a bit more research on your part, but it will be worth it in the end. These are Toyotas, so buying used should be a viable option; just make sure the SUV is mechanically sound and look for an extended or original factory warranty and you'll be fine.