You're not improving any cash flow here, just adding on another bill that will suck your cash flow dry for the next 5 - 10 years if you let it, then of course you'll have more desperately needed upgrades.  

Unless you plan to reinvest at least some of the profit from the sale of your current home, you'll be back to cutting hair in the next year or so when your funds dry up. 

When it starts to look rough with areas of drying out and serious curling and splitting I replace it before it leaks.

Often the HOA Master Policy covers some or all; you/your insurance pays the HOA deductible; the lower unit pays for any upgrades they installed.Water damage that presumably occurred over some period of time could very well initiate mold growth if it was not promptly and properly dried out.

Plaster of Paris (takes a little practice) for the deep areas, finish plaster for the top, both dry fast and sand smooth, you're on your way.

I would think so, its very dry and sunny.

For example, when the entire town of Paradise, CA burned down a few years ago, many non-admitted insurers became insolvent leaving their policy holders high and dry.

It's cheaper to soak and cook dry beans over eating canned beans, just saying!

3bd/2b upstairs, 1400 sq ft with attached 2-car garage; stairs lead to finished basementfinished basement: 900 sq ft, 1bd/1ba where bedroom doesn't have closets; but is fairly large spaceheating/cooling control: not sure if top/bottom have separate controlsmeters (gas/water/electric): just 1 for whole houseLocation: schools are 4/3 rating, but on top of a hill with Bay Views. 0.5 mi from 80E freeway (one downside is you hear freeway from yards but not from inside house)accepted offer price: $906K with 20.5% down, requires $9K of dry rot repairs, and $5-$15K to move washer/dryer connection lines into garage so that both top and bottom units have laundry access.  

You don't need a CG - you just need someone to do the work; dry wall, painting, carpentry and plumbing.