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.

It is pretty cool that you were able to get that property after such a long period of time from the first time that you found it. 

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.   

It has different rules than a service animal, but is nevertheless not considered a pet and can land you in hot water for treating it as such.

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? 

The cool thing is most of the time there is an alternative exit strategy that will still lead to profitability in the long run. 

In my mind, Portland has many similar advantages to San Francisco - geographic constraints to spreading (rivers, mountains), difficult development requirements, a young workforce and better than national average population growth projections, and a "coolness" factor with tech workers and millennials that one can't simply create by declaring oneself a tech hub. 

The only reason I have 48 hours advance notice is that one particular group of people have to let a big pressure vessel cool down before they can work on it.