1. Nellie Etta Currier - Dec. 15, 1897, Loveland, Larimer Co., CO (divorced Dec. 1932)
2. E. H*** - Jan 1933, Kiowa, CO

In 1908, his father, Daniel (and his sons) formed the Loveland-Estes Park Automobile Transportation Company.  The company was the first to operate motor vehicles to the park, and used Stanley Steamers as their automobile, and may have begun the route several years previous to the company's incorporation.  By this time, F.O. Stanley (one of the brothers who invented the Stanley Steamer) had established the famed Stanley Hotel in Estes Park, CO.  Mr. Stanley soon formed a similar transportation line, and the two companies shared a tent in Estes Park until buildings could be erected.  The roads were very poor, often flooded as it wound right next to the river through a rugged canyon. 
 Will managed the company for a number of years.  There appear to have been many adventures for the entrepreneurs - one such adventure is noted in the Loveland Reporter, July 2, 1908:

MAKES RECORD TRIP FROM LOVELAND TO DENVER

Will Osborn of the Loveland-Estes Park Auto company, made a record run from Loveland to Denver, to Long's Peak Inn and return to Loveland last Saturday from about five o'clock in the morning to ten-o'clock in the evening. Mr. Larimer and a party of six friends arrived in Denver from Chicago last week and wished to go to Estes Park by way of Loveland, and desiring to see the agricultural district between Denver and Loveland, phone for Mr. Osborn to meet them in Denver with an auto.

The distance covered was over 200 miles and they were delayed on the trip by having a puncture and stopping about two hours to repair the tire.

There are also reports of several accidents, some of serious nature.

Will moved to Denver after the company was sold.  He became an auto mechanic there, and one obituary notes that he was the first President of the Auto Mechanics Local, No. 606, and was a life member of Loveland B. P. O. Elks lodge.  He was survived by his second wife, and three children.