Based on some properties I've looked at the mortgage/insurance payment would be about $500-$600 so combined with my rent I'd be paying around $1100/month.

You will pay mortgage insurance either way for the privilege of putting so little down on properties. 

The home needs a major rehab including roof, soffit, bathrooms, kitchen, flooring, drywall, painting, A/C, water heater, most likely electrical and plumbing.

I would ask your insurance company, I know my insurance company had some issues when I had 4 names on a lease that didn't share a last name for a SFH. 

Personally I'm keeping the one rental I have now in my name and using a well known insurance company with a solid insurance policy to cover me.

Im in a similar situation with a municipality, but if you are able to cover health insurance through the service, that makes the transition out of the traditional W-2 much more feasible and also covers all of your bases.  

He also said that I will get dropped as a client if I hold the insurance company to their $1k deductible they quoted me.

I'm going to have the outside vinyl sided which will be the only cash I have left in the deal.Actual Monthly Expenses:Mortgage Principal & Interest: $380Monthly Taxes: $68.92Monthly Insurance: $63.75Cap-Ex: $95Vacancy/Credit Loss: $47.50Property Management: $50Total Expense including estimate for vacancy and cap-ex: $715.17Rented @ $950 per monthExpected Cash Flow: $234.83Living Room:Master Bed/Bath:Under the cardboard box in the pictures were about a hundred cigarette burns in the carpet...Between the 5 people and 3 dogs living here when I bought it there wasn't a blade of grass in the back yard:Still haven't done the vinyl but it sod does wonders and it only took 1 pallet. 

I'd sugggest: https://www.bbb.org/central-texas/business-reviews/plumber/pro-tech-plumbing-and-construction-in-killeen-tx-90005982

You could also take loans from retirement accounts or life insurance policies.