I have yet to complete a walk-through of the property and see what renovations may be needed (potential for HVAC and interior, but from my understanding the roof and windows were replaced within the last 7-8 years).

Will the roof need to be replaced within 5 years?

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. 

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

And if you can, try to avoid racking up more debt on your cards while you’re paying off the loan—it takes some discipline, but it's definitely worth it in the long run!

I think the A frame idea works great for this setting, but some have said the A frame style steeper peaked roof works better. https://www.instagram.com/redtail_cabins_adu/

Guy who inspected gave some report asking to fix the issue on roof and if it’s not addressed they will terminate policy by January,15th.

Double check any cap ex you might have coming in the next year or more there so you can plan to set that aside (boilers, roofs, etc).

The home needed a lot of work including roofing, windows, siding , kitchen, baths, and mechanicals.

I then hired contractors for plumbing, electrical, roofing, and HVAC upgrades.