Painters, Siders or Roofer rec in Chicago

My building has two dormers that are clad in untreated wood, and I would like to seal or stain them, or open to other options.  The dormers, one on each side of the house, are a good 40 feet up, and the roof has a pretty decent slope.  I talked to a painter who said he would have done it himself 10 years younger and dumber.  

Should I look for a roofer, who might take it as a side project?  Or try another painter?  Or perhaps a siding company? 

Any recommendations?