Buy a property (1-4 units).

Buying an investment property at 21 shows amazing foresight and financial responsibility.

I think Collin is being a little tongue in cheek with the Boone's Farm comment.I work with a local, large wine store, wait for their semi-annual sales when they compound discounts and buy 2 cases of each (white & red) for the largest discount.Basically I'm setting out wine that retails for $11-12-13 that I have paid $7-8 a bottle.  

But they had to jump through a dozen HOA hoops..eventually, the building got stricter on short-term stays.For single-family homes, if you can snag something with a scenic deck or quick access to popular spots, you’d be surprised how many travelers pay a premium for that “living like a local” vibe.

I have no prior investment experience but after living in Paraguay, and reading some books about real estate investments, I think I'm ready to buy my first property.

Both units are approximately 400 sqft, "yurt-style" cabins with large decks.

As someone new to NYC, I'd appreciate insights on:The current state of the UES market in this price rangeWhether buying makes financial sense for a 3-year timeline versus rentingThe pros and cons of co-ops versus condos in the neighborhoodI'm particularly interested in hearing from those with experience in the area, as I'm looking to make an informed decision.

Starting with a $100K headstart is more than a enough to buy a new primary home. 

You mentioned buying a fixer upper with your HELOC and now are talking about a 20% down payment.