You also need to get title insurance too. 

Can anyone recommend any good resources or rules of thumbs for coming up with a ballpark estimate for property insurance when doing a quick analysis of a rental property?   

So you are essentially looking at 1500 a unit for a 3bd- 1200 a year for insurance seems low, to be honest- unless you got a quote for this prop 2160 a year seems low for taxes 1200 for lawn/snow a year is high... this winter was bad, and it also depends on if you have a driveway etc or just street parking Closing costs- you can get a good faith estimate from your lender- they may be a bit higher Also, you want to consider if you would be inheriting tenants.. or if they are way below market rent, 

Contact your local welfare office to insure they will cut off her S8 income if she violates her lease.

IDK exactly what your taxes and insurance are, but this looks to me like you need $5500 a month in rent to be break even.

Add up the cost of your mortgage payment, taxes, insurance, vacancy, repairs, cap ex, and management if you will use it.

What will it cost for cap ex, management (when you grow and want this), regular maintenance, taxes and insurance (if not in mortgage) vacancy allowance, eviction costs, turn around costs to make the units rerentable. 

Big thing holding me back is getting over hurdle of health insurance for my family as well as 401k.

I have attached photos of what I would consider pertinent parts of my purchase and sale contract regarding realtor liability and mediation, as well as the part on risk of loss/insurance that reads something like if there is damage that is returned to it's former condition prior to sale, the Purchaser can accept that or has the option to terminate the contract... as I was not made aware of the damage taking place, I never had the option to terminate the contract, or accept if the condition was returned to it's original form.I emailed my closing attorney and I'm waiting to hear back, as well as waiting to hear back from my realtor as they were going to contact the seller's realtor to discuss this.Is this damage something I definitely should have been informed of?

Without knowing the Tax Rates for the area of Interest, I would use $500 / Month for Taxes, and about $125 / Month for Insurance, and another $100 for MI, leaving you about $1275 for P & I (Principle & Interest).