Check the major components, like roof, siding, windows, driveway, HVAC, electircal for good condition - cosmetic upgrades (paint, flooring, even kitchen cabinets) are cheaper than those big hitters!

Maybe an a/c is slightly more expensive if you have to cool a larger area and of course flooring and roofs are tied to the size of the house, but Capex wouldn’t be 4x as expensive in the second house, right?

Same with asphalt roofs, versus tile roofs, versus condos.  

I believe they may limit it to 3 or 4 unrelated people under one roof which I think is a state law but I would call the city zoning office to confirm.

I know a lot of investors who are selling all of their properties that are 15+ years old; for fear of upcoming repairs (roofs, A/C & boiler).

BUT, there are exigent circumstances like plumbing leaks, fire, or police emergency.As for civil penalty, I have never heard of the police charging the property tax paying landlord a fine for such a violation.

The email stated that the underwriter has assigned an action for me which read as follows: "The shed is in poor condition and needs the following repairs: rotten soffit and fascia, roof replaced and trees at the back cut down to prevent further damage."

It is exactly for those reasons that my tenants will have a roof over their head one year from now, in a building that I still own.

Leaking sink or plugged toilet.

And like Lesley said, everyone needs a roof... it's a basic need.