The house has a finished roof, exterior windows and all of the weather wrap, but no siding and no interior pictures (assuming it would be at the most, dry-walled inside). 

I have several houses in Orange County, CA which I would like to replace the windows.

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How are the windows and what are they made of?

For me a sign in the window of the property and word of mouth advertising by friends, family, neighbors and of course yourself seem to provide the results desired.

I told my wife that I would not throw $20-30k out the window in taxes and penalties to buy the property.

I've had some success in those windows....

Brtan, I believe the value of the 50% rule is in the idea that expenses will be 50% of rent so when PI exceeds that the investor should look closely at what will be coming up, i.e. new roof, furnace, siding, windows etc.

Yes, you can depreciate existing personal property in the house using 5 years accelerated MACRS depreciation, including:AppliancesCarpetingOther "removable" flooring (not adhered or glued down)Drapes, blinds, window treatmentsAwnings attached to houseFancy lighting fixturesYou will need some support for your values, either an appraisal from a used appliance dealer, printout of Craigs List ads, etc.You can also depreciate land improvements over 15 years: landscaping next to house, fencing, sidewalk, driveway.You need to subtract all of this from the total costs, and depreciate the residual over the standard 27.5 years.

We'll paint the entire outside of the house, minus the roof, the windows and any awnings.