The quality of work by a crew of people depends on each individual's quality ethic and skill level plus that of an overseer/foreman. Easy question here, I would opt for the craftsman with an eye for detail.

Are they both licensed and insured? Have you seen their work? Have you checked references? Have they each priced the work completely? Have you selected any and all products and or finishes? Without knowing the home and the full scope it is tough to tell if the thee time frame necessary. Chances are the 40 year company may not have his entire crew on site at the same time all the time if it is a refresh as he will have other projects going on I am sure, same as the individual/helper company.

SInce you posted this in the Old House I would check what their experience level is with that area. There's a big difference in working on a newer say 1960's home and working on an older pre 1900's home.

But the one who takes 4x longer is yet to be determined! Gotta show up every day... Plus I deal with contractors who aren't licensed all the time. They're usually the best ones!