The first house that I bought was 17 years old, 3 br, 1.5 bath, brick ranch house with hardwood floors, Andersen windows, ceramic tile baths, gas heat and a brand new roof. 

Slate roof or even Spanish tile.

I own a roofing company in Denver and a separate gutter company there too. 

But the other side of the coin is correct - the downside, and it can be huge, is potential assessments from HOAs who aren't solvent enough for new roofs or roads or maintenance.

Estimated cost for remaining changes (all new electric, drywall, tile, fixtures, cabinets, roof, doors, windows, heat pump, some siding, and fencing.

It is a older non rehab property but things are straight and roof, plumbing, electrical are all in good working order.

It seems to me though your short term objective is to get the HOA to take immediate action on the roof.

My heart rate goes through the roof as I have about $90k in equity in that house. 

Just make sure you keep enough in an emergency fund in case a roof or furnace goes out. 

I hopped on the roof with the garden hose to defend the property (even though initially it was contained) when suddenly an ember spread to a palm tree (that had been neglected to be trimmed for years) that instantaneously atomized/vaporized into hundreds of embers and spotted fires on several homes.