You should consider Vinyl Siding. I had a clap board sided house and I
ripped it all off. I put up insulation board and then vinyl siding. I
also have a brick home with wood soffit. I ripped the wood out of the
overhangs and replaced with vinyl soffit material. It was an easy job
for the Do it yourselfer and I'll never have to paint it again! It can
also help with ventilation if you use the ventilated soffit material.
If you paint, you have to keep repainting every few years. I did this
to one of my homes 10 years ago and the other 7. They both look as good
now as when the job was first completed. I never regretted it. I would
deffinately do this to any home I ever own.

Just my two cents
Pat