One day you are riding high, the next day a ton of bricks is landing on your head.

Someone I knew did get ride of his car and was moving around only Lyft/Ueber.

I am hoping to pull from your experiences and avoid the pitfalls of getting taken for the proverbial 'ride' as I am just getting started with my first REI multi-family in Bayonne.

Or maybe just ride her coattails on her deals until I can get off on my own? 

In my opinion, a turn-key property won't return very much so you might as well put your money into an index fund and let it ride. 

The thing that I keep thinking about is that it's a bike ride from the ocean and that will never change.

I'm all for more metal roofs, look beautiful and very durable even for hail.

If someone is looking to hold for 20+ years and has the finances to withstand a turbulent ride, then they'd prob be ok..  

Having that base will make pursuing your goals in real estate way easier.You can certainly use Uber to fill the gap while you are looking for the IT job and as a great way to continue driving for dollars (between rides), and getting to know the market. 

Enjoy the ride!