THE 1903 SEASON
During her inaugural season, the Eastland showed no signs of instability but performed well under her targeted speed, being able to achieve only 19 miles per hour. Her water ballast system likewise did not perform as was hoped. The Eastland spun or damaged blades on her propellers many times on the sand bar off South Haven and in the Black River. Since the Jenks Shipbuilding Company was responsible for the performance incentive clause in the Eastland's construction contract (and Jenks himself was now a shareholder in the Michigan Steamship Company), the Eastland returned to Port Huron on September 22nd for the winter-spring season for modifications to enhance her performance.

A McCreery ventilation, or air-conditioning, system was added, as well as an Ellis and Eaves induced draft system. While the McCreery system was one for passenger comfort, the Ellis and Eaves system would provide the additional speed required by contract. With the additional weight of these modifications, the Eastland's draft was increased. Since she was already having difficulties with her entrance to South Haven, the ship's machinery was rearranged to improve her draft from the 1903 season.

Unfortunately, all of these modifications added additional weight and reduced her draft, thereby reducing the Eastland's metacentric height and her inherent stability as originally designed. Only now, she was really built for speed.

THE RACE WITH THE CITY OF SOUTH HAVEN
The Eastland returned to South Haven on May 9, 1904 to join her running mate, the Soo City. The Soo City was an older, smaller, single-screw wooden ship that was to be used mainly for cargo transportation. For 1904, the Eastland still sported her original dark-green hull paint and upon inspection, was allowed a passenger capacity of 3,300 under the command of Captain Dority.

The Michigan Steamship Company began advertising the Eastland as the fastest ship to Chicago. The owners of the City of South Haven contested this claim, as their ship had outperformed the Eastland regularly during the 1903 season. The challenge was accepted, wagers made and the date was set. Excitement grew throughout South Haven, with the general public betting on the race's outcome in one form or another. That day finally arrived. Each ship was clocked as it left South Haven and when it arrived in Chicago. The Eastland won handily, at a speed slightly greater than 22 miles per hour! The newly crowned 'Speed Queen of the Lakes' had regained her throne.

1904 INCIDENT
All would not continue as well the rest of the year. The Eastland experienced periodic problems with her stability while loading and unloading cargo and passengers.

On Sunday, July 17, 1904 a near catastrophe occurred while the Eastland was heading for Chicago after leaving South Haven with approximately 3,000 passengers aboard. It was a hot day, and a crowd of about 1,200 passengers congregated on the hurricane deck for relief. After traveling about 1.5 miles into Lake Michigan and shortly after clearing the sand bar, she began listing to port by about 12 to 15 degrees. The water ballast was adjusted to correct the list, but then a worse list to starboard occurred, estimated to reach 20 to 25 degrees. Water began coming through the aft starboard gangways, flooding the main deck with a foot and a half of water.

After relocating the passengers, whose concentration on the starboard side of the ship had likely contributed to the listing problem, and shifting the ballast again by adding water to the port tanks, the list was soon corrected. If the ship had capsized, she would have continued over until she rested keel up in the water. The loss of life would have been devastating.

This incident occurred in full view of South Haven and the public was alarmed. On July 26, 1904, a request was made to lower her capacity to 2,800 souls. Another incident occurred on Sunday, August 5, 1906 with 2,530 passengers on board, again caused by a concentration of passengers on one side of the ship. It is important to note that other than these few incidents, the ship's safety record was consistently satisfactory.

CHICAGO-SOUTH HAVEN LINE
More modifications were performed on the Eastland in the winter 1904 and spring of 1905. Since the Eastland was only making one cross-lake night trip per week, 49 aft cabins were removed. Her hull was also repaired due to sustaining damage from a twice daily scraping of the South Haven sand bar. A fourth pair of lifeboats was added, as well as a bright new coat of white paint on her hull.

These changes put the Michigan Steamship Company is great debt, from which it did not recover. The Eastland was sold to Robert Blacker, president of the Michigan Steamship Company in December 1905 for $100,000. He reorganized the company as the Michigan Transportation Company on December 21, 1905. For the 1906 and 1907 seasons, Blacker made arrangements with Dunkley-Williams to co-partnership as the Chicago-South Haven Line. The Eastland and the City of South Haven ran under the steamship line operations for these years.

SOLD!
Before the 1907 season commenced, a group of investors from Cleveland contacted him with interest in purchasing the Eastland for a reported $150,000. Blacker accepted the offer and paid off Dunkley-Williams with $20,000 to break their co-partnership contract. The Cleveland group formed the Lake Shore Navigation Company, hiring A.H. McLachlan as captain. The Eastland left her winter home of Manistee, Michigan and journeyed to her new home in Lake Erie.