The good guys pay me money for insurance, I promise to release my team of ruthless lawyers on anyone that sue them, the patent trolls see my scary lawyers and don't sue. Doesn't that work?
Lawyers can make a considerable amount of money, any disruption to the Patent Trolls' game will severely reduce their numbers. These Patent trolls, as you said, are often lawyers and by tying them up in court you are costing them profitability. Every non-settlement forces them to go to court and actually fight.
This is how the courts work: Out-of-court settlements are frequent and are preferred as it saves a Judge's time for real cases, however mass submission and withdrawal of suits are seen as a waste of the courts time and effort. A fair amount of cases end up in front of a judge before settlement, if these end up being withdrawn (and the judge will know it's withdrawn not settled) you're going to be in bad credence with a judge. Pissing off a judge is a big no-no. Patent Trolls will be pissing off multiple judges, which is like putting a shotgun in your career's mouth and pulling the trigger.
An insurance agency that fights patent trolls would be ideal. Offer $X amount of legal fee coverage for $Y a month, get a few talented lawyers and a fair amount of paralegals. Once word gets out, the majority of the work can be performed by paralegals (essentially everything up until you're standing in front of a jury-or-equivalent can be performed by paralegals) as no troll will want their time tied up. Eventually, only Trolls with a fair-case will fight, you then have 3 options to give your clients: offer them your lawyers' services/suggest settling/wish them good luck elsewhere. It would be a sort of no-case-no-extra-fee's deal.
Lawyer's typically bill by the 6-minute interval, and frequently charge 100's of dollars an hour. In fact 1-2 billed hours is typically a lawyers daily pay, and they may still have 6-8 hours on top of what they're billing clients. If you start consuming these lawyers time, their profitability drops, especially considering they require settlements for their pay. They're invested in the 'easy win', which isn't conducive to fighting a drawn out case. If companies actually start going through with the court battles, the payment is potentially delayed anywhere from 3-months to 3-years.
Don't a lot of trolls actually have valid patents that read on whatever it is you do?
If this worked, why wouldn't Microsoft just "self-insure" and never, ever settle a patent claim?
In this instance, Microsoft's attorneys risk alienation too by playing the chicken game, and they don't want to do that.
How it could work is to find a judge who thinks patent cases like this are ambulance chasers, and then ensure that all the suits against you are relocated into her court. If you have a friendly judge then it becomes much easier to play chicken.
How exactly do you do this? I've been wondering. It seems trolls are able to get these cases heard in disproportionate numbers by a strange little puppet court down in east texas that has become famous for being troll friendly. (and indeed seems to have based its entire local economy around it)
The trolls don't want to enter a losing battle because of the cost (even if they're in the business of litigation, time spent suing one company is time that could be spent suing another). Also, losing would damage the validity of the patent for future cases. (In my understanding, that is. IANAL)
For example, if USV is typical and 1/3 of venture-backed companies are being attacked by patent trolls, then the premiums for this insurance would have to be extremely high -- enough to cover a third of the cost of defending a typical case.
Also, if the patent troll is suing a bunch of companies you're insuring based on the same patent, you could attempt to combine the cases, thus consolidating the defense costs. This works because patent trolls work by firing off lots of very similar lawsuits, each for a small enough amount that it's economical to settle. That's what keeps their costs down; such an insurance policy would let the defense leverage the same economy of scale.
Here is where insurance can actually increase litigation: a person without assets often isn't worth suing but a person with the deep pockets of an insurance company can become worth suing.
I still think it's good idea to create an anti-patent legal pool but it's important to understand all the angles...
The problem would be maintaining a reputation as someone willing to pay for long legal battles.
Essentially, if you could show that any patent-troll would face an SCO vs IBM situation, I think you could have some plausible deterrence.