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.

They update all the bathrooms, kitchen, plumbing, electrical, and replace the roof.

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.

With all this I do see opportunity in certain pockets that could not have been able to get a year ago.In saying that people that have cash and can get lending could clean up soon.My personal opinion tho. 

that is HOOD rat written all over it.. just another west coast investor who does not realize that low end cheap property in the mid west for out of state investors is super high risk.. only locals can make that stuff work.. you may want to reassess your strategy.. your going to get your clocked cleaned if you keep looking for those kind of deals.. 

Structural & functional items usually need permitting (framing, roof, electrical, plumbing, etc), whereas flooring and landscaping do not. 

 $99/night + $75 cleaning fee and $300 refundable deposit for a 2/2 1300 sq ft log cabin in a private community with lake views and steps away from the lake shore.

Another example is it wont be their fault if the house has gutters and leaves clog them up and water backs up into the roof because it was not stated they were responsible, or if the property has a fire place and the house burns down because the chimney was not clean sweep by them or you before use because it was not designated responsibility.

Just so happened to ran into the maintenance guy when I was checking out the property and he let me do a walk through in one of the units being cleaned.

After that, my PM spent time in cleaning the property and listed the property around early/mid Jan.