Initial comments 
At first pass, this looks quite good. It's comprehensive, well sourced, and well written, and seems generally ripe for promotion. I've made a few tweaks as I went; feel free to revert any with which you disagree.

Here are a few quibbles that I couldn't immediately resolve myself:

I'd suggest splitting the lead into two paragraphs for readabilityperhaps at "Increased expenses and decreasing ridership"?
"with two railroad stations in operation, one on the C&O; line and the Union Station just west of the C&O; station at the junction between the C&O; and Southern railroads"  I found this part of the sentence hard to follow at first glance; maybe break this off as a second sentence: "two railroad stations in operation. One was on the C&O; line, and the second, the Union Station, was just west..." Am I understanding the meaning correctly in this rewrite?
"Development of the streetcar system"  I'd suggest breaking this long paragraph into at least two for readability (Perhaps at "this continued until...")
Route Description  split large paragraph for readability
Two statements here that it would be better to fix in time per WP:REALTIME for clarity in the long-term:
To address these issues, the city has begun planning and analyzing various methods of public transportation for implementation within Charlottesville, one of which includes the development of a streetcar system. ("in the early 2000s, the city began...")
 though no concrete plans have been developed or implemented ("as of 2012")
The track gauge given in the infobox needs a source