ie, wind damages the roof and that lets in rain that damages sheetrock, floors, furnishings,...   

Look up 'Margin vs Markup if you're curious.)So if my Plumbing Sub-Contractor gives me a bid of $20,000 for your project, I will not tell you that number, I will just have a price of $25,000 for plumbing on your Bid/Proposal.Note: It does come out close to even for you........my plumber gives me a steep discount because I give him $100k worth of work each year......

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

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

With a dozen properties over 25 years I have yet to spend a dollar on a roof or painting a house exterior.

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.

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

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

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.