Ken, as I tell my graphic design students (over and over, hehe) you have to establish "heirarchies" of information. Simply put, this means you decide what is the most important information, secondary, tertiary etc. Then use larger, bolder type for most important info, smaller, lighter type for secondary info, etc. Colour contrast is also an important factor. There is more contrast between white and orange for example, than there is between yellow and orange. Condensing type is considered a last resort. Never condense type more than 85%, as it begins to distort. Serif type can be condensed a little more than sans serif.
So, here's the critique from the "teacher". The lozenge heralds have been nicely simplified, which works well and has a more modern look. But, the type is too condensed and too close to the edge. "Ohio & Florida" is the most important information and should be in white. The tagline would be in yellow. "Transportation Company" also has a more modern ring to it, as many modern railroads offer trucking, logistics and even ships. CPR went to CP Systems. If you're looking for a shorter word (which never hurts) you might consider that.
Also, most modern railroads are well known, which means they don't spell out the whole name in the logo. Examples are UP, CSX, CN. Maybe you could play around with that idea.
Ok, class dismissed.
Val