There is not much first-hand information concerning this since cowboys stayed busy just doing their job, without much time left over for writing. However, one guy did document his experiences and adventures and did a darn good job at it, too! His name was Andy Adams, and his journal was published under the title 'The Log of a Cowboy.' I have a 1969 edition from Airmont Publishing Comany, Inc, New York, but if you cannot find this copy, try Amazon.com or Bookrags.com for a second-hand one since they carry books currently out-of-print.
I loved this book! I would have a hard time picking out any one particular thing more important than the rest, but what immediately sticks out in my mind is his description of forcing cattle to ford a rushing river and the fact that cowboys would cover long distances for many hours just to get together around a campfire at night and cook doughnuts!
Another tip: Try a cross reference search on the Internet concerning black cowboys. There were many young Negro men who struck out West to seek a new life, and some became very famous. To name three: Nat Love (nicknamed "Deadwood Dick), Bill Pickett, and Henry Harris. A silent movie called "The Bulldoggers" features Pickett "doing his thing," but documation of such sort is rare to come by.
The life and work of the cowboys was really quite difficult. The cowboys came from the lower classes of society and so they were not treated very well.
When they were at "home" they lived in barracks, not in individual homes. They were generally fed by the ranch, not all that well. The pay was low.
Of course, they spent a lot of time out on the range. There, they would round the catttle up (the cattle would just run loose on the range) every spring to brand the new calves.
They would also go on cattle drives where they drove the large herds of cattle to towns that had railheads. Typically, there would be approximately one cowboy for every 250 cattle on these drives, so there was a lot for the cowboys to do. There were many dangers from such things as crossing rivers or, especially, from stampeding cattle. Men were often killed by stampedes.
Cowboys came from all classes of people, they came from Yale graduates, doctors, lawyers and all walks of life, some came for their health and some came for the excitement, take Theodore Roosevelt for example, a small glasses wearing slight of a man with bad health became a Cowboy and worked his way up to the President. life for a Cowboy on the plains was not an easy one and unlike the movies portray the Cowboys and Indians rarely met and the advent of " cowboy diplomacy" came before bullets however there were more deaths from fighting against other ranchers than agains Indians. the food was edible, the weather was nice (most of the time) and the livestock didnt ask too many questions, for the most part it was an uneventful life punctuated with a lot of excitement at times.
My father had 2 great uncles who herded cattle from Wyoming to Northern Texas in the mid to late 1800's. The winter snows provided prime grazing for the cattle in Wyoming while Northern Texas provided the market to sell their livestock. The life of these pioneers was hard. The unpredictable weather was a big factor because the cattle were not able to go to markets and stock sales until mid summer through the fall. The ranchers usually would only be able to sell the cattle that were born in the previous spring. The changes in the seasons often brought thunderstorms which could be fierce at times. River crossings would cause obstacles for the drives because of these storms and flash floods were very common. The cowboys might not even see a storm, but the flat land would funnel the runoff their way without warning.
The cowboys were paid on their successful delivery of the cattle to market. For this reason, they took extra care in their livestock so the majority would make it to the sale. They usually recieved a percentage of the total profits. Since there were so many cattle, it benefited the cowboys to look after one another so all the cattle would survive the drive.
Common illnesses took a toll on cowboys. They were far from doctors, usually more than a day or so. The common cold could turn into Pneumonia or some type of infection and the cowboys would be forced to find another hired hand from a nearby town to finish the job. The rancher usually did not know everyone who was driving his cattle to market. He had only a couple of his "trusted" hands on the trip. These trusted hands were usually his sons or other family.
Thiefs would become more prevelant the closer to the market they traveled. The herds were so large that it would be quite easy for someone to steal several head of cattle. For this reason, half of the cowboys would keep watch at night and shoot anyone who they viewed as a thief or threat. The laws of the "old west" applied. It would be easy for thiefs to steal some cattle and sell them at market to give themselves a profit.
Cowboys were ruff and rugged. They had many obstacles to overcome. Most were single, young men who had no other way to make a few bucks or they just wanted the adventure. Cowboys could make a name for themselves on the great plains and this news got around. A name as a cowboy could get them more work as a possible drive boss. Drive bosses recieved a bigger percentage of the sale and more prestige.
I hope this helps.