Painters, Siders or Roofer rec in Chicago

[Geoffrey Klein]

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?

[Geoffrey Klein]

@John Warren  - that was something I was considering.  The rest of the house is sided, so it makes sense, but do siding companies take on small difficult jobs?  Or would I be looking for a brave handyman?

@Matthew McMahon - the property is in Chicago Lakeview.  The homes are close together, but there is 3 feet of space and on one side maybe easy ladder setup in a neighbors backyard (if i get friendly with them).  The idea of going to a Benjamin Moore store or painting supply store isn't a bad idea...  I'll try that as well.  

Just called a bunch of those options, roofers, siders, painters to get quotes.  See if anyone is willing to take it on.