Thanks for the detailed post bro. can ask where u stayed in NYC? trying to decide between hotel or airbnb, cos not sure if airbnb is safe there. didn't realize it was illegal in NYC
did you visit the factory outlets?
I stayed here for 5 nights. not cheap and very small room. clean with branded fixtures for the bathroom but that's about it - you're paying for location.
Hilton Garden Inn New York Midtown Park Ave
airbnb is still available in NYC (like in SG), you can try and im sure many have. at immigration the officer will normally ask for proof of your itinerary like flight and hotel bookings. it is not in their authority nor interest to enforce short-term rental laws but if you catch an officer on his bad day, you may just give him a chance to make things difficult for you.
factory outlets are damn far away, it's like a full day thing (2hrs there, 2hrs shopping, 2hrs back) so we did not "waste" our time since shopping was not our absolute priority. instead we visited discount chains like TJ Maxx, Marshalls, Nordstrom Rack and Century 21.
these chains sell mainstream brands like lacoste, polo ralph, tommy hilfiger, calvin klein, dockers, nautica and such brands on discount. like $20~30+ for polo t, $10+ for t-shirts, etc. selection may not be as wide and varied compared to outlet but we were happy with what we found. we spend an hour or so here and there in between our sightseeing.
Century 21 is particularly good especially for ladies. you're talking about
haute couture like christian louboutin, gucci, versace on discount. so instead of $1,200 for stiletto, you pay maybe 700?

for guys you have nike/reebok as well as expensive leather shoes or shirts and suits, so it's some serious shopping.
prepare your credit card!
https://www.c21stores.com/stores