Yes, it is the R. L. Polk's City Directories that usually always gives the wife, occupation and address, if it was given to them. Also, when the husband has passed away, if the widow is listed by her own name, you might find the reference "wid" with the name of the husband. It may even list the names of children, who have reached majority, or are in their last year of high school, showing the same address as their parents and designate their occupation as "student."I've seen a few city directories from other publishers but prefer Polk's format over the others for research purposes.
The listings in the directories from 1952-1962 for Hugh I. OSBORN, listed with a wife Amanda (her middle initial was found both as a "C." and an "S."), lived at h 5664 SW Cheltenham Drive, and his occupation was salesman. In some of the directories it didn't list any employer, but in a couple of them the employer was listed as "Shulton Inc." I looked for the name of the company in the alphabetical listing, but didn't find that business listed in the Portland City Directory. I didn't have a clue as to the type of business, so I didn't even try to look at the classified section, under type of business.
Since you didn't mention the name Harold in your first posting, I went back to see if there were any men named Harold or Harry, and I found a few listed, in some of those directories, during the same time period.
OSBORN, Harold L. (Pauline L.) (Osborn's Clnrs), h 3504 SE Harold Ct.
OSBORNE, Harold K. (Lois) driver, Jones Lbr, r 6225 SW Virginia.
OSBORNE, Harry W. (Marie), h 115 NW 22d Pl.
[Research Note: No occupation was listed for him, but in another directory, this man was later listed as a salesman for R. L. Polk & Co.]
OSBURN, Harry S. (Margot E.), claim investigator, Portland Traction Co.
In 1955 there were two men named Harold OSBORNE living on the same street name, but at a different house number, within about 3 blocks of each other. One was listed as Harold OSBORNE, no middle initial and no wife, with an occupation of laborer at r 5623 SW Kelly Av. The other man was listed as Harold K. OSBORNE, no wife listed and the occupation of driver for Jones Lbr Corp.
[Research Note: This may have been the same person, who just moved and his information was put in twice, once for each address.]
In the 1960 directory, I found a listing for a Howard I. OSBORNE, wife was Monta C., his occupation was physician for the Portland San. & Hosp., home address of 5933 SE Yamhill.This same year, Hugh I. OSBORN was also listed with wife Amanda S., and Hugh was still a salesman for Shulton Inc, and stil living at h 5664 SW Cheltenham Drive.
So you now have two men with the middle initial of "I" to see if either matches your family history stories.