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

You pay a local licensed contractor wIth a good reputatIon to accompany you for a second look .have him look over all the structure and systems etc.. have him do quick quotes on issues he sees on a legal pad as he’s walking through each room have him check the wiring the roof the furnace the plumbing .

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?

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.

Neither the other driver nor their insurance company can demand that they are only responsible for paying you, if you get the bumper fixed.