What kind of paint and siding are you using in Buffalo? I had a house painted with Behr point, but it only lasted 5 years and now it needs painting again. Is this because of the extreme temperature changes in the area? Is there a better paint or siding to use?

I'd suggest benjamin moore aura for exterior. Its expensive but seems to hold up. Other wise use vinyl everywhere. Less maintenance :) 

I'm flipping a house right now and we opted to put on vinyl siding rather than repaint the wood. Painting in the winter sucks for the contractors - siding they can at least do the prep work and cutting indoors when it's cold. Also vinyl siding is low maintenance and buyers like that. 

Paint doesn't last much more than 5 years unless it's on cedar shingles then it may last longer, Behr is good paint. 

Vinyl Siding is a better option in my opinion, It looks great and is pretty easy to power wash yourself. skip the paint.

Spend the extra cash and upgrade to a new siding material like vinyl.