Your statement “always a surface lines town” is unclear. The surface lines were always very important to Chicago, but the L and steam/commuter railways were (and are) never as insignificant as you imply.

It does not take a “double bus connection to get anywhere” in the Red Line extension service area. Every single bus serving the Red Line extension area currently terminates at the Red Line 95th Street terminal. That’s a single bus connection.

“Reaching the city’s border” is an arbitrary distinction. The justification for extending the Red Line is to facilitate access to jobs for a part of town that needs it. Most of the trips after extension will still require a bus transfer — albeit in many cases a much shorter one. Where the city limits are is really irrelevant.

Red Line extension plans have not been on the books for “100 years”. At best it’s been 50. More realistically less. That’s a long time but no need to exagerate. For most of the past 100 years, the Red Line extension area had been well served by frequent “rapid transit” style service on the Illinois Central railway. Nowadays, the former IC service has become a commuter railway with less frequent service and the population center of the area has shifted westward so that the proposed Red Line extension route serves it better than the IC would.

What stats do you have to show that the Orange Line extension terminal area has had a “significant” economic decline since the late 1980′s, and what relevance does that have to extending the transit line (the Red Line extension area would be considered an astounding success story if it were to come up to the level of economic activity that currently takes place in the Orange Line extension area!) Ford City Mall is arguably less economically vibrant than it once was, but the other real estate along Cicero from 63rd all the way to 79th is arguably more vibrant (albeit heavily auto-oriented in design). And the industrial/manufacturing uses to the west are all still quite active.

Finally, your description of the Circle Line is entirely inconsistent with my understanding. You call it a “solution in search of a problem” yet (in this case honestly) for the past 100 years, a major problem with transit in Chicago is that no inter-connectivity has been designed into our city’s rail system apart from the very concentrated 1897 Loop terminal. The Circle Line builds in direct, weather-protected, transfer connections with every L and Metra line serving downtown, and does so by leveraging mostly existing track with a minimum of new construction. This represents the greatest bang for the buck possible to solve these longstanding network interconnectivity problems.

Secondly, your assertion that the Circle Line “serves a corridor of middling job/population density and limited growth potential” is completely inconsistent with reality on both accounts. First, it would dramatically enhance service to the Illinois Medical District — connecting it to all of the existing CTA and Metra lines in the city with one direct and quick transfer. IMD is the largest job center in the city outside of downtown, and generates a high volume of student and visitor traffic in addition to all of its workers. Second-greatest concentration of jobs and activity in the city is hardly “middling”. The Circle Line area has also seen tremendous economic activity outside of IMD and is poised to support significant future economic growth. North/Clybourn, Wicker Park, Near West Side, Pilsen, Bridgeport, Chinatown, and South Loop are among the most economically vibrant and growing neighborhoods in the city, and access to and between them all would be significantly enhanced with the Circle Line. And there is a tremendous amount of land remaining available for development and redevelopment in all of these neighborhoods — particularly the area to the north of IMD, near the United Center, which could support very intensive new development. It could be argued that the Circle Line is the key ingredient to ensure that the future redevelopment of these neighborhoods proceeds in the most urban and transit-freindly nature possible, with a much higher future transit mode share than it manages today. What “other proposals” could stack up to this?

As for BRT, there I agree with you that prospects are dim, although the reasons go beyond the points you mention.

Extending the principal cross-town rapid transit service (the Red Line) for “the last five miles” — it reaches the city’s north border, but stops well short of its south — should be a high priority. The largely low-income and transit-dependent far south side has lost countless heavy-industry jobs. Having gone there last weekend, it takes a double bus connection or infrequent commuter rail to get anywhere, compounding its distance from the N/NW “favored quarter.” These lines have been on transit plans for 100 years; the Orange Line “extension” proposed was even part of the original proposal but got value engineered out. (In the intervening 20 years, though, the original terminal area has declined economically, and I’m not sure whether it can really come back. The Yellow Line extension is interesting and restores access to a major job center, but pretty small in the grand scheme.)

Given the distances involved (12-16 mi. as the crow flies from downtown), there’s no way for surface transit to serve the same need. That said, there’s no local match money available for anything, anyways.

The Circle Line looks interesting on a map, but it’s an expensive solution in search of a problem. It serves a corridor of middling job/population density and limited growth potential, and offers minimal rider time savings. Other proposals to enhance downtown distribution, or improve crosstown buses, would offer better time savings and TOD potential.

Oh, and BRT? Impossible, since IDOT jealously guards its sacred freeway lanes, and Morgan Stanley is holding our parking meters hostage until our great-grandchildren come around.