For a rental, I can see replacing or repairing a unit being deductible as expenses and property improvements.If I am going to be wealthy someday, I do not want to have to wait two weeks for someone to fix my AC when it goes out in my house, and I do not want this for my renters either.

Although the nightlife and culture (museums/food/music) was a great and calming change from the busy metro area, I felt isolated.

Assuming you continue to live modestly, you will come out of college more wealthy than when you entered it.

This is same question why in US we have culture of tipping when other country do not , also why in Us there are just so many added layer fee for attorney , legal and sort of.To be quick , higher commission in US happened because American way of doing business is not efficient, there are layers for law, legal and attorney fee.

The thing is, some people can make money in any market if they can find the right opportunities, you can make lots of it but those opportunities don't exist for everyone.The reality is that, at 7% interest rates and 0 - 3% appreciation, the average investor can't become wealthy quickly with a little bit of cash flow.

Remember wealth is built not flipped. 

My personal expectation is that N CHS continues to appreciate into a wealthy suburb/satellite over the next ten years. 

Consider leaving NYC if you are unhappy with the demanding hours.NYC has a tough work culture - I lived in NYC for 35 years of my life and I been traveling for the past 3 years as a Nomad.People work less hours and are happier in other areas of the world. 

Either the culture just didn’t match or it just didn’t feel right.

I hadn't hoped for rates of 5% from a wealthy doctor, but would love to shave anything that I can off of the cost to do business.