What would the mortgage payment be with taxes and insurance included versus your current rent payment? 

What I am saying is, you need to do what works for you, not what makes your realtor happy.If you can't buy a house in your market with an inspection contingency, you had better figure out how to insure the house gets inspected one way or the other.

Here are my quick numbers on the deal:$1,600 gross rent-$570 ish for mortgage-$160 for management (10%)-$128 for maintenance (8%)-$128 for CAPEX (8%)-$128 for Vacancy (8%)=$486 month or $5,832 a year (12.9% CoC)Then you still need to budget for Taxes & Insurance, this would drive down your return further.

What should I be asking of the contractor to be certain they are insured properly & feel confident they know what they’re doing?

The question is would this be a legal use, as long as I have proper documentation, or would this be seen as intermingling funds?

Can anyone direct me to a tool to estimate insurance for single, multi families and/or commercial property?

What are typical expenses other than loan,insurance and tax ?

Keep in mind your numbers aren't taking into account insurance, taxes, capital expenditures, or property management.

Without my degree I wouldn't have my job earning a solid W2 and providing retirement and insurance benefits for my family.

If you do not pay at closing of auction you will be liable for 20% of property value plus fee's.You will receive a sheriff's deed without warranty, you may not be able to get title insurance on the property.