I also won't be driving as far for work so I'll have lower expenses and more time to read, research and study real estate. 

If the rent is greater than the expenses by ~$150 a month, I don't see why not to do it.

Maximize expenses inside the business as the tax code allows. - Anish

Its a Triplex with an unfinished bonus room with possibility of making a studio rental.Current Income: $2755Mortgage Expense: $2600Current mortgages total $349K  (1st+2nd)Owner is open to creative financing.  

My Dad is a contractor so all of the work will be done in house so I'll be able to avoid contractor expenses.

I don't want to give away any secrets on a public forum, but there are multiple studies/surveys/data from sources such as realtor.com that show Chicago in the top 10 cities to flip properties w/ median income of $76K per flip.  

However, most of that income is offset by expenses to reduce taxes.

I learned to cook because the foods I liked are expensive in restaurants.

PMI is an unwanted expense that can be the difference between cash flowing and not cash-flowing, so getting rid of that should be a priority.

Here are some rough numbers for my expenses so far:Purchase price: $1+$25 recording feeBack taxes: $2300Legal fees: $3000Rehab estimate: $5000Tax assessed value is $66k.