The strategy would work  better if it were your primary residence, but it becomes more difficult if you're trying to convert a SFH to a true two-tenant duplex.1) You'd must likely be violating zoning (Unless area was zoned MF), so you'd have to hope the conversion flies under the radar.2) Utilities is the biggest hurdle, as a SFH only has one water, electric, and gas meter.

Even though in some places one organization collects taxes for multiple taxing jurisdictions....for example the county may collect for, the county, the city, the school district, the hospital district, the community college district, the water supply, the noxious weed control district, etc, the individual entities may have lists too they would give you.   

What DID help were the sources listed and their referral to our next source.2) The ADA.gov (Americans with Disabilities Act) is a part of the United States Justice Department and defines the standards in the country with regards to those with disabilities. 

This is a standard strategy that investors use and yes, lots of lenders can help...but lots will NOT be able to help...or if they do, they will have restrictions...like waiting 6 months. 

Here are the knowns:Rent per tenant: $750 (this is below market value due to deferred maintenance, I believe $1,000-1,200 is more realistic)Property taxes: $900 per yearLandlord insurance: $1,000 per yearLandlord pays water/trash: claims to be $125 per month (will ask for proof)Landlord is in charge of snow removal and mowing lawnThere are 5 electric meters, each tenant pays their own (landlord covers hallway and outdoor lights)What I plan to ask for is the copies of the leases, copies of the utility bills, and copies of bank statements showing the tenants are actually paying on time.

If it is a covered loss, it's a covered loss, and you will get what your policy states.If I have an insured event, like a backed up sink that causes water damage in the unit, it's not going to matter to my payout whether the renter had a renters policy or not.

How do I know things like the cost of water and sewer, loan points, ARV (without an agent to pull comps), Capital Expenditures, or any other number of items without fully engaging the seller? 

Part E1 might violate what's in most standard leases about an agent of the owner having access to the unit to show to prospective buyers or tenants.

As a buy and hold real estate investor, can you charge a tenant for repairs if they do not take precautions during a freeze by opening cabinet doors, letting water drip, covering outdoor spigots etc. which cause pipes to burst?

The deal has to be good, at least by your standards, experienced or not.