Should I stay Or Should I Go?

[Latifa Al Latif]

My lease is up March 2020, I’m prepared to purchase but looking for input. I have 2 options: A. Buy a townhome in my current area (Naperville, fairly affluent suburb near Chicago with great schools) or B. Buy a small Multifamily in Chicago.

Option A: My son doesn't have to change schools. I'll be saving on rent. I could get creative and find an investor for deals in Chicago to start my REI journey.

Option B: Find a great school in Chicago (Southside, Chatham), buy a small multifamily, have tenants pay you the bills and save my work income for another property and in a year or two, move back to Naperville.

The dilemma:

Option A: Naperville is expensive and as a poker dealer, my income remains $67/k without increase. And I work 60 miles away. My money is spread super thin, and it’s starting to get stressful.

Option B: Chatham isn’t the safest neighborhood. I can save 90% of my paychecks for the year with a small MF.

What would you do?

[Jim K.]

Originally posted by @Crystal Smith:

Originally posted by @Latifa Al Latif:

My lease is up March 2020, I’m prepared to purchase but looking for input. I have 2 options: A. Buy a townhome in my current area (Naperville, fairly affluent suburb near Chicago with great schools) or B. Buy a small Multifamily in Chicago.

Option A: My son doesn't have to change schools. I'll be saving on rent. I could get creative and find an investor for deals in Chicago to start my REI journey.

Option B: Find a great school in Chicago (Southside, Chatham), buy a small multifamily, have tenants pay you the bills and save my work income for another property and in a year or two, move back to Naperville.

The dilemma:

Option A: Naperville is expensive and as a poker dealer, my income remains $67/k without increase. And I work 60 miles away. My money is spread super thin, and it’s starting to get stressful.

Option B: Chatham isn’t the safest neighborhood. I can save 90% of my paychecks for the year with a small MF.

What would you do?

My first priority would be what's best for the kid's future. Can you get your child in a school in Chicago, private or public, equal to or better than Naperville?  If yes then pull the trigger and look for the small MF in Chicago. Note:  There are some excellent Charter Schools but you'll have to apply early. Regarding safety in Chatham; there are plenty of nice pockets. 

I can't accept that argument, with all due respect. "Good schools are most important for your child's future." It was simply not true in my experience. I went to high school in a place called Horseheads, NY. In Horseheads, they literally make T-shirts that read, "Where the hell is Horseheads, NY?" There is absolutely NOTHING outstanding about the academic challenges you get in a place like that in upstate New York. And I graduated somewhere around 100th out of 350 graduating seniors.

So I went to state school, the SUNY system, actually not a very well known school in the SUNY system at all, SUNY Oswego, after bouncing around elsewhere in the SUNY system for the first two years. I excelled at Oswego. I did so well that I was offered full PhD fellowships to Brown, U. Michigan, Rutgers, and U. Pittsburgh actually offered to appoint me as a lecturer after my first year of grad school there.

So I went from a largely BS public high school in upstate New York to full funding for an Ivy League doctorate.

Kids either want to excel academically or they don't. Moving into a tony neighborhood to give a child the best possible future in a  supposedly highly-rated public high school is largely a fool's errand, a game that we all play nowadays and almost every kid loses. I was an indifferent high school student. That didn't mean I was destined to be an indifferent college student. There were 340 applicants for my PhD program at Brown. Six candidates were accepted, four decided to attend. I'm sure plenty of them went to nicer high schools than Horseheads High and much more highly ranked colleges than SUNY Oswego.

And in the end, none of all that academic achievement mattered anyway. I went into real estate and I now work maybe 16 hours a week on average in the education-related W2 job I still hold largely in order to get easier traditional bank financing. What I'm doing almost full-time now is buying houses in C'class neighborhoods, fixing them up myself, and renting them out. I spent most of yesterday cutting upward into the bottom of a hundred-year-old cast iron toilet discharge with an angle grinder. Hard to imagine an Ivy Leaguer doing that? That's the real world for you, and here's the real kicker...I'm pretty sure I'm much happier now than I would have been otherwise.