I read your article and was amused by the batanalysis you did, but I think your reasoning lacked thoroughness, or was optimistic to the point of foolishness. Here's my two cents to add to your thoughts. Well, make that a lot of cents (no pun intended) as this ran longer than I originally thought.
Real world masks only have recently become less effective in the age of security cameras running 24-7, but bad guys still use them to generate doubt for the court case. Psychologically speaking, people who are not autistic nor have photographic memories are prone to forgetting things under stress - and being a victim of a crime generates sufficient stress.
Much of the old time goofiness you refer to harkens back to the era when comic books were designed to be silly. There are too many arguments nowadays of 'what is canon and what is not' to support releasing humorous content like that, not to mention the moral advocates would go into a tizzy if violence was not depicted as having gravitas. Besides, a comic would not have a wide enough target demographic if it was seen as too childish.
Bruce Wayne, Party Animal
Swanky charity balls will always happen in an era of insurance salesmen, robbers or no. The only real backlash they will get is their insurance companies hitching their rates up - in order to be truly elite, one must have both the money for the dinner plate, and the insurance money to cover your visit. The problem with trying to be an idiot and well versed in pop culture is that logically you'll be one or the other. Being "in the know" may mean that your agent (or your fair weather network of friends) handles the details for the truly idiotic party animal. Too many quips and such will ruin the idiot profile. Besides, the truly social elite sets the standards, not follows them, and even social gaffes earn time in the limelight giving excuses for the gaffe and blaming the masses for their lack of vision.
Bruce the Playboy
Socialites wouldn't compare notes, not because of story convention, but because of jealousy and one-up-manship. Lies and rumors would churn around the girl of the hour until it was her turn to man the rumor mill. Nobody would be able to sort the chaff from the wheat, unless it was a conspiracy theorist, whom very few take seriously. Even the 'bestest' of friends would play up their encounter in an effort to not look left by the wayside. This lifestyle would also get dangerous for Bruce if the girl is particularly stubborn, offering massages or other 'remedies' for the headache. There could also fly rumors of inadequacy, cowardliness, or general lack of manliness on his part if the headache conspiracy did win through. All of which would ruin his playboy image.
Mission
I've always bought the whole story about the cape and cowl being designed to strike fear into the hearts of those he's about to pound, because it makes sense. If he's been pounding baddies left and right, even in a ridiculous costume, that's going to give him street rep - and maybe thoughts of what he could do to them if he wasn't encumbered by the costume. Surprise trinkets give him the fear hesitation that can make or break a fight by itself. First impressions are the strongest and usually the first glimpse the baddies get is a eerie shadowy profile backed by lightning. Batman's stealthy isolating tactics also work wonders for unnerving the baddies, too. All of which works to his advantage in the fight and in his rep.
Bruce could buy off all the baddies off the streets, but then he'd have to subsidize all the fast food workers, shelf stockers, and others who just barely make it who would give themselves over to his generosity to not pay rent or scrape by ever again. Then there are the street bums who would take his money, blow it, then steal other's stipends just because they 'need' more money to waste. This isn't even touching the inflation problems that would occur when everyone has money and the supermarket only has a limited supply of stuff. Or addressing the issue that some people actually choose that lifestyle for whatever reason.
The game theory bit makes sense too. What works for a do-gooder works for a bad guy. Ridiculous costume = fear in street cops. I remember in Batman Beyond (episode or movie, I can't remember) that they said the Joker's whole purpose in life was to make Batman laugh. No Batman, no Joker apparently. Some people just love a challenge regardless of the consequences.
Young trauma, like phobias, are deeply rooted and difficult to unseat. Batman retaining this is one of the humanizing character traits, not an artifact of it being in a comic. Terrifying and assaulting the baddies is his childish lashing out at those who look like the ones that killed his parents (not that I'm pretending to be a psychologist - I took a college course or two but that's it). The circumstances were nicely crafted to give a realistic scenario of a guy, who under other circumstances that we'd jail and asylum-ize, that has made it his duty to beat up baddies.
In the cartoons at least, I've never seen any of the court cases of the generic baddies that they round up - there is a very good chance that the judges are much like the detective who hates Batman and doesn't trust him. It could be that they send the baddies to jail then release them in the morning - lack of evidence, accusations of planted evidence, what have you. Also remember that Batman is only one guy in a large metropolis that seems to see a lot of crime with many crime lords. If word leaked out that a percentage of the crooks get caught and beat up by a crazy only to not spend much time in jail - that will put a roof over their head and food in their mouths every night without losing that feeling of control over their lives that a lengthy prison sentence would carry - it would attract more and more obvious baddies hoping to get caught by Batman repeatably, rather than chase them out of town. Bruce may be beating up a pool of the same Joe and Bob individuals plus or minus a crime lord's particular bunch every night. Those Joe and Bobs likely start early with petty stuff to fund their nights out of jail, or to add to a stash, then move on to the flashy 'come and get me' stuff later on.
Batman probably avoids the big dog baddies, not because of Time Warner, Inc., but because Wayne Enterprises, or Bruce himself, likely has a share of the other companies. Beating them up and making them look bad would be bad for stocks and eat away at Bruce's crime fighting funding profit margin. Selling his shares beforehand would be a big red arrow connecting him and Batman. Besides, the headquarters to most of those other companies are spread out worldwide, not sequestered in Gotham, and therefore outside his stomping grounds. This is why I'd imagine most superheroes sticking to one city - it's easy to chase a bad guy and corral them to a dead end that you know about (and hope they don't) rather than chase them to their own bolt holes where they disappear. This was addressed nicely in "Teen Titans in Tokyo" and if I recall correctly was briefly touched on in "The Dark Knight" (the logistical problems of having him be in two places at the same time while he skips town to be Batman elsewhere).
As I said above, there is a psychological reason that you could apply if you wanted a real world excuse as to why he only targets the little guys. Besides, until recently with all the crises, big corp baddies were shadowy and far removed from most people's thoughts (which made them all the more insidious when they had the whistle blown on them); day to day robbers, druggies, and muggers make the news commonly. This puts Batman's help more visible 'on Main Street', rather than a once in a while help 'on Wall Street'. It also fiddles with the class war concept - he's not helping the middle class as much as he's helping the lower class - the upper class having their own defenses from most street issues in the form of bodyguards, gated communities, and insurance on everything. Just because he's not assaulting the upper class exploitation of the lower class does not mean that he's on their side.
Effectively, Wayne Enterprises is the epitome of what big business could be and Bruce is the definition of benevolent dictator over his own company - at least he was in the movies. In that sense, the big company behind Batman the comics tries to show that not all big business is bad - luring people into the sort of ease it takes whistle blowers to wake them back up again if indeed something foul is afoot.
Other comics
Other villains may or may not know anything about their peers, so even interrogating them may not be very effective. Not all universes had an organization of villains, and I doubt that bad guys would publicize their plans to anyone, let alone potential rivals. Both the names you put down are only first names, add last names and the chances of both words having that effect is exceedingly rare and obviously concocted with her powers in mind, which is on a timeline outside the scope of most comics which are rebooted every couple of decades.