Rents continue to climb as well but likely not enough to keep up with increasing monthly mortgage payments when considering interest rates and soaring property values.There are 2 main schools of thought when considering investing in an expensive market like Long Island.- Robert Kiyosaki, Grant Cardone, and similar thinkers believe its best to invest in markets with higher cashflow while renting where you want to live.

The short version is that you want a strong and diverse job market, low unemployment rates, a growing population, low vacancy rates and new development, affordability/cost of living, real estate laws and court system, good schools, and low crime.Check out the videos from Dave Meyers with BiggerPockets.

My son currently lives in the townhouse b/c he is going to school and works in the area.Since he is young and starting out in life, I would like for him to only cover the basic costs (taxes, HOA, utilities) just enough for me to break even (I believe that will put him slightly little lower than market rent rates). 

Also, jumping into real estate straight out of high school is amazing! 

A certain school district? 

The house is in a great school district.

I currently have around 20k cash for a down payment and that is steadily increasing so I want to pull the trigger soon.I'm interested in Fort Wayne for a few reasons:- I have some family in the area (they won't be involved, but have some general knowledge of the area)- Decent schools- Low crime- Airport- Low pricesAny advice or connections are welcome as I am completely new to this.

But RC builds in areas with good schools and those homes rent well.

The final size of the house will be about 2500sqft, 5 bedrooms (each between 11x11 and 15x14), 2.5 or 3.5 bathrooms, in a strong A- neighborhood (600k-800k houses with amazing schools).

They aren't going to magically improve and start abiding by the lease terms but I think there is definitely a possibility that the situation gets worse.I think that's a good point.