Here is some additional information to ensure success:First, tenant screening is critical, focus on creditworthiness, rental history, and stable income.

plus Midwest so a stable REI market.Here is the problem I see.  

It is hard because you feel like you are falling behind, but you are so right that I need to ensure that my foundation is stable.

I can't retire on these small assignments.

—> Ideas to get cash: Save, sell something, borrow against your retirement account, work another job, ask for seller financing, start a side gig and grow that.

I've done an excellent job at meticulously tracking everything, so I feel comfortable with the "monitor closely to see what a stable asset looks like" strategy.

I've now asked 100s of times, "Do you know a retired real estate Agent?"

But the question is whether one can actually achieve the proforma cash flow on older properties with a less economically stable tenant base.Based on your picture, you appears fairly young.My advice is buy properties in quality locations think long term 10 to 15 years - slowly and safely build your portfolio - equity and cash flow will increase over time and in 10 to 15 years you may become financially free.People talk cash flow is king but one can NOT generate financial freedom cash flow with $250,000 or $500,000 invested (equity).Even at a 10% cash on cash return, one needs $1.2M invested to generate $120K a year $10K a month.You want property to be self supporting so it needs to cash flow but once that is reached the focus in my opinion should equity growth which increases net worth.

I guess the place to do probates is in the dying fields of Florida, Retired and heirs back up north.

If the property has long-term and stable tenants then a shared electric meter could work.