Always appreciated. Even more appreciated, though, would be thoughts on the above questions. Are they fair questions, and if so, what are the answers?

I've seen losing campaigns morph into winning ones after two or even three cycles. But only because those involved re-doubled their efforts and learned from their mistakes.

Obviously you are far more competent and professional in your evaluation.  I too, as you note, am concerned that huge amounts of concern is raised and expended on the web, with little being shown on the ground.  

The netroots have an ability to get up a concern.  We need to find out that a candidate is not just doing net stuff, but is also doing all the other things to win.  Sort of a "better candidates bureau" for up-and-comers.  I have contributed several times over the last several years to people, and been burned once or twice. Not that I expect to win, but in some cases like Bean in IL-08, I have been really annoyed with how DINO she is.

As someone who grew up in one of the counties in what's now TX-28, and who's been in every county in the district (well, except for Zapata, and frankly there's not much reason to go there) I think I might be able to shed some light.

No idea on points 1, 2 and 5-7.  I don't live there anymore, and even though I follow the district (family still lives there) I couldn't tell you what the ins and outs of the campaign itself were.  

On #3, it's true that Ciro didn't have a lot of cash before the netroots kicked in.  There was speculation early on that Richard Raymond would join the race.  Raymond is also from Laredo and is a fairly popular state senator.  There are other politicians in SA who were thinking about the race, and that probably hurt Ciro in the fundraising department.  Essentially, the district was forced to line up either behind Cuellar or behind Ciro.  They just didn't line up early enough behind Ciro.  There were also other high profile races in San Antonio, which doubtlessly hurt fundraising.  The areas of San Antonio where the high profile races were are not affluent in the least.  Politicking in the area is very much who you know, who you've worked with, word-of-mouth, and believe it or not there's a lot of family ties involved also.  

On #4, though, I believe Cuellar improved his standing not solely because he was the incumbent but because of a sense of pride in Laredo and Webb County (and to an extent Zapata County).  Cuellar's voting record goes out the window when it comes to a local, homegrown boy in Congress.  I may be completely wrong, but as far as I know, Laredo has always been split into 2 districts, usually being matched up with portions of the lower Rio Grande Valley, and sometimes partitioned up with parts of the "brush country" that makes up the area between the border and San Antonio to the north and the Gulf of Mexico to the east.  Simply put, Laredo hasn't had personal, homegrown representation in Congress.  And keeping that meant a lot of the people there, no matter his voting record.  

One thing to understand about the South Texas border area is that it is largely forgotten.  The only attention the area gets comes from the after effects of NAFTA...whether it's the improvement in highways or the influx of money, or the maquiladoras moving across the border to Mexico.    Cuellar brought home the bacon to Laredo and is a source of local pride, I'm sure.  It's odd to think of an American city of 200,000+ being "forgotten" but that's largely what Laredo is.  Growth along the border is far faster than other areas, yet this area is woefully ignored.  I cannot emphasize enough the personal pride involved in having direct representation in Congress.  Think "Local boy done good" on a much larger scale.  No matter what anyone could say about Cuellar, he was/is Laredo's shining star.  As loyal as people are in South Texas, Cuellar's status is locked up even further because of that.  It's a mix of pride and family that doesn't really look at ideological distinctions between candidates.

The presence of the 3rd candidate (in my opinion) did not affect Ciro at all in any appreciable way.  Victor Morales is a perennial candidate these days, and while we think fondly of him for taking 44% against Phil Gramm in '96, Morales has not shown the guts to stay politically involved or the tenacity of a hard fought campaigner.  His story in '96 was truly inspiring...a schoolteacher criss-crossing the state in a white pickup, with maybe a tenth of the resources of his GOP opponent comes within 6% of a win.  However, he carpetbagged his way into this race by way of his parents, who live in Pleasanton in Atascosa County.  I think people saw that and if they weren't directly related to him, probably didn't think too much of him.  

I hope that helps..not that it's concrete answers or anything, but then again, we were going up against an incumbent with a rabidly loyal base.  That's a fight most often lost, no matter where it is.

Thank you for a very informative post. Here's a little feedback:

Essentially, the district was forced to line up either behind Cuellar or behind Ciro.

Understood, but wasn't that the case in the last election? That's in the nature of a primary -- people pick sides. My question still is: What happened to the ~50% support that Rodriguez had in 2004 in the period before the netroots stepped in? If he was "walking dead" (as Kos put it) up until that point, that means a huge number of prior supporters either abandoned him for some external reason, or were not properly cultivated.

Also understood that Laredo was hugely behind their local guy... But it still seems to me that Rodriguez surely knew that going in, and in retrospect would appear to have had no (effective) strategy to undercut that massive base, or at least to offset it in some way.

I guess at the root of my post is a hunch (and it's just a hunch) that certain obvious problem areas may have been allowed to slide, or just not anticipated by the campaign.

Looking at future races, like Lamont v. Lieberman, it behooves all of us in the netroots to try to help the on-the-ground campaign fully assess and anticipate the particular challenges of that race, to avoid another money drain with no payoff.