Basically you are better off leaving units empty than rent to someone that is not at least a decent tenant.We use quickbooks for managing the financials.For tenant maintenance items I am old school and just use a notes to-do app that is shared with my lead handyman (who is leaving me in December: Ugh!).

I have been taking martial arts for decades. 3rd degree black belt.First you need to quantify martial arts school.

I’d consider moving especially If you have job prospects in the new community, and I’d certainly recommend researching it well before considering moving there in terms of life style, outdoor activities, night life, schools if you have or may have children, travel accessibility (highways, airports) sports teams if this is important to you, etc.

For starters what's your Location A,B,C,C+ D areas etc, school districts, economies, diversity of jobs, specific population amounts etcCondition/ Repairs needed year of homeProfitability Criteria Anything else you care to add. 

The parcel was by a school, restaurants, and other businesses.

Have family throughout DuPage and was thinking out there or central-western Cook thinking there's probably families trying to get into good school districts and not a lot of SFH rentals in areas like Wheaton/Naperville/Downers Grove but am finding the cashflow doesn't make sense for 90% of the deals I analyze.

@Yakir Sheli you may find something good in Deer Park if you are patient (flip opportunities + pretty good schools)

I also worked with the local medical school as our facility was also part of their residency program. 

high school and college kids, retired folks who want something to do part time, or to just pick up some supplemental income.    

These cities tend to command quality tenants, and they have great schools.