People were panicking about their roofs collapsing and willing to pay almost anything to get someone up there to shovel them off.

If it is recorded as built in 1920, that is what the insurance will be based on.The most valuable update with regards to insurance is the roof. 

Got insurance involved and use that money to remodel the entire inside, and add a new roof.

since as part of the project you are going to need an architect and civil engineer, I recommend starting with them and ask them who they have worked with for zoning.

Old properties aren't a bad thing as long as you account for the big four- HVAC, foundation, roof and sewer.

Tone, pace and the exact words matter.

So the major issues in a house are a foundation issue or a structural issue, the next tier down would be a mechanical issue like Electrical, Plumbing, HVAC, then roof - which isn;t an issue a new roof is very common in a fix n flip, and then the outside facade: Brick repair, driveway repair, brick pointing. 

Yep you never know when you are going to need to refi or quickly sell a property.

Purchased for $69,000, it needed a full rehab, including a new roof, plumbing, and modern updates inside and out.

Purchased for $69,000, I tackled everything from a new roof to interior updates, transforming it into a move-in-ready home.After months of surprises (and a few headaches), I sold the property for $145,000.