To Chris' point, you can find lower options if you handle some of the management responsibilities.

The tenant pool can be lower end in Winnipeg but if you invest in the right areas it will often qualify for CMHC financing in terms of affordability. 

You’re able to learn the basics of a real estate investment with lower risk and build equity at the same time.Because you're in the military, you'll be able to enter a property with 0% down which means you can leverage your money way more effectively. 

Which is why I pay more, for less cash flow in highly desirable areas.In high income areas, rent is a lower proportion of income so therefore your tenants have a higher capacity for paying higher rent because rent is less than 20% or even 10% of their income.

If it turns out that the tenant clogged the drain, we give them one warning and after that we charge them.

I am in Milwaukee, very hot rental market.Whenever you have an issue like this, think with an XLS and project dollars, for example:- 2 months lost rent: 2 x $2000- 5% lower purchase price: $15,000 

TurboTenant offers a maintenance program for $149 annually; they will respond to tenant issues, troubleshoot, assign to a pro, and charge your card on file (unless it's over your set amount, then they will call to confirm).

I understand they purchased their property bit earlier at a lower price, but the difference shouldn't be so significant.

I am in PA and yes, it is legal to charge late fees to your tenant regardless of Section 8 subsidies or not, provided the tenant's lease allows for them.

I agree, criminal charges have to be filed.