The you drain all of your savings unless you have more and how will you pay your taxes and insurance?

There is no such thing as a "guarantee" only the perception of.if it's a concern in your offer, find out what it would cost to carry a bond or insurance product for the seller. 

I'm hiring a property manager and the management contract requires a waiver of subrogation in favor of the property manager. I think I can get a policy online with the other requirements, but this waiver seems to be m...

Key things to keep in mind with your numbers are:Rent should be > PITI (principal, interest, taxes, & insurance) + maintenance + vacancy + capex + property management fee. 

Any recommended providers I should run quotes through for homeowners insurance?

Principal, interest, taxes and insurance. 280k with 20% down at 7% = about $1500 a month for PI.

Insurance wrote a check for much lower than what contractors were bidding for restoration/remodeling. 

If you have any questions regarding the real estate purchase (negotiation) process, the loans you might be qualified for (low downpayment or low interest rate options), or the insurance you may need for the purchase I can answer any of your questions.

Cover half the mortgage/utilities/insurance/taxes etc 4.

I double "co-hosters" in most markets are getting 25-30%.If property management interests you I would suggest you become a licensed and insured PM company to increase your credibility.