Listen to the contractors. You won't do better than fiber cement siding like HardiPlank. Won't burn, rot or crack and it's straight when it goes up and stays that way.
It's low maintenance, and it needs to be painted. The idea of zero maintenance is attractive yet elusive, much like the unicorn. In other words - there is no such thing as a maintenance free. In addition, there shouldn't be. Maintenance, at the very minimum, is a yearly inspection and cleaning, with whatever minor repairs and caulking needed. That's how you avoid the big bills down the road.
Supposedly it can be patched with topping cement, although I've never done it. It is one of the more dense and durable sidings. It's most likely to be damaged during installation. As in most things, making the patch invisible is the hard part. Since the siding has to be painted, it's easier to hide the patchwork.
Admirably. It holds paint better than wood. A paint job will last you longer on fiber cement siding...as long as you take care of the yearly maintenance.
HardiPanel. Be well aware that it is not a continuous "skin" of "fake stucco". They're sheets of "fake stucco". Those seams are the weak point. I usually work in a half-timbered look with fiber cement battens over the seams which fits well with the stucco look (at least in northern climates). If you try to just caulk the exposed seams you'll never be able to hide them. Pay close attention to where the seams are and incorporate them into your design.
Cedar does have a life span, but if its a few shingles or so just replace them, its easy to do and Re- Stain. Sure a contractor wants a " Job" that is worth $ to him, But if it isn`t total crap siding id wait.
1st, this time of year prices are highest, second, you have not specified the Rot damage of total worth. Make the decision yourself, contractors want " jobs". I have all Cedar in your heat zone of 5 and won`t go hardi crap.
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