The outside if my house is Spanish stucco, painted over with what appears to be an oil-based paint. In certain areas the paint chipped off or looks loose (rain probably infiltrated) I live in NYC and it is winter time: is it better to remove the chipped paint and leave the stucco unpainted (bc the paint won't cure well when it is cold) or wait until spring to start the repairs? The damage is not great, there are a few areas and a few cracks. Thanks for the help!
Widen the cracks to an inverted "V" shape and fill with a good quality latex caulk (do this on the next mild dry day). Water wont penetrate a sound stucco wall but the cracks may allow it to seep through. If the forecast calls for warm weather, 60 degrees or better, for 2 consecutive days than it is alright to do some painting. Wrap up early afternoon before it gets cold.