I don't know enough about your rentals to determine quality, location, or layout, but I suspect my numbers are pretty close.However, your utilities are pretty expensive in the winter.

I am about to lose my car my place to live basically my life.

do you cash flow in month 1 if your rent is $1200, and your expenses for that month are $1198? 

They should have the option to install a security alarm at their own expense.

My plan is to funnel the rental incomes from all three properties, along with my W2 income, back into the HELOC while covering all expenses from it as well.

Tons of returns set this system off: errors, no income lots of expenses, disproportionate expenses, etc.When all that is done, IRS has a budget for how many returns they will put in the audit queue.

I can’t think of an expensive subscription that doesn’t provide an app.

You get a deduction for the contribution, the gains grow tax-free and as long as you use the proceeds for health-related expenses the funds come out tax free as well. 

On the flip side, if you've got a bunch of Section 8 tenants living in a building that's in a neighborhood where a lot of the tenant base has good jobs, high credit scores, and are generally reliable people, you've got the most risky tenants in that tenant base and that ain't what ya want.

I found an area I felt comfortable living in and I bought a house with an FHA loan.