I'm guessing that this is not a trick question!
The last time I was in NYC was in 2007 and things might have changed since. But in 2007, if you spent $150 or less in the one transaction, there was no sales tax charged. If you spent over $150 in the one transaction, then the state taxes would apply.
If you have time to head out to Woodbury Common Outlet outside of NYC, then you would be able to combine outlet shopping and NYC experience in the same trip. I've been to NYC three time now....never made it out to the Common YET! Always too busy shopping in the downtown area instead.
Orlando outlets are much like every other outlet. If you find something you like and in the right size, then it can be a bargain. It can be challenging finding something you like.....and then finding it in the right size.
I've always thought that if the full retail shops are on sale, then the shopping in the retail malls can be just as much a bargain as the outlets.
As to which is better?
My recommendation on shopping when on holiday anywhere is that if you see something you love, have the budget for it and are happy with the price, get it! You never know if you're going to come back....and you definitely don't want to come home thinking I wish I'd bought that when I had the chance to...!

