I agree. I do not view the wealthy in general as an "enemy." 

I agree that the accumulation of wealth often corresponds with the production of social value. It is interesting that you bring up the issue of rent-seeking as a problem but not that a lot of "rent-seeking" is perfectly legal and is often a component of accumulation of wealth even where part of it would be attributable to socially valuable production.

For instance, I am an attorney who (among other matters) litigates personal injuries and worker's compensation claims. There is a component of general social value that is produced through my activity: aiding in the resolution of disputes and serving as a helpful piece of a functioning legal system. However, there is also a "rent-seeking" component of my job, I am looking to transfer wealth or prevent the transferring of wealth from an opponent to my client. The degree of my compensation, or the ability of me to accumulate wealth, corresponds more strongly to my rent-seeking ability than that of my ability to generate general social value (because I am paid by my clients on the basis of being able to resolve disputes on more favorable terms for them, not by the judicial system generally). Thus, in relation to my social value created, I (or rather, the firm that I work for) is likely overcompensated. The same is true in many other extremely lucrative industries, such as finance.

One quibble with the mode of analysis for taxation. The way to evaluate the impact, positive or negative, of government spending, would be the effect of the spending vs the average counterfactual effect of retention. Thus, for impact analysis, we would not be comparing the utility generated from government spending to the cost-effectiveness of a marginal dollar to a Givewell-endorse charity, but rather the utility generated by the counterfactual retention of the funds by the taxpayer base. In any case, that bar is much easier for government spending to clear.

I could imagine a few things:

1. Pledging may have some combination the effect of (a) actually increasing people's lifetime donations to effective charities and (b) causing people to advertise giving they already were going to do. To the extent that a pledge is b rather than a, getting someone to pledge the same amount as you is not double your impact.

2. Many of the people who you cause to become pledgers might have become pledgers later, thus you probably just accelerated their pledge, greatly decreasing your actual impact vs if you cause someone to pledge (and this pledge causes them to donate more rather than encompasses donation that would otherwise happen).

3. There's a possibility that you could anchor someone to donate less. Potentially someone could see your celebrated 10% pledge and view that as adequate, lowering their donations. Here, there is a risk of harm from the pledge.

All that said, I still think the pledge is an awesome way to promote and normalize effective giving.

It is really great to know that the pledge allows pledgers to use their judgment as to what organizations qualify as highly-effective organizations. In light of this, I may make a 20% pledge.

We all pay for the government's ability to protect the wealthy by yielding to the government its monopoly on the legitimate use of force. In a "state of nature" most of those with the skills or luck to accumulate wealth would either enjoy it fleetingly or pay significantly higher costs for its retention than taxes under governments. If a system of law and order enables the lucky to be so much better off regarding their wealth, it strikes me as quite fair that the unlucky should share in the benefits of society as well.

I understand we may not be as far apart on policy, but this is why I bristle at the "necessary evil" framing of taxation.

One of the things that moved me away from the libertarian view of all distribution as violence is the notion of government in any form as protecting the wealthy against existences in which there would be much more violence and in which they could not be secure in their wealth and comfort. Essentially, no matter how self-made, one's wealth is almost always enabled by a functioning form of government. It seems reasonable for those whom government enables to be very wealthy and comfortable to require some contribution so that others might have minimal comfort or opportunities. 

It seems as if the potential of the damages could make the vast majority of defendants "judgment-proof" (meaning they lack the assets to satisfy the judgment).

I wonder about the ethics of an organization that had the policy of financially supporting people (post-bankruptcy) who made potentially extremely high EV decisions that were personally financially ruinous.

You have defined socialism here quite broadly, which may be unhelpful to discussing it as it can mean anything between

a. A market-based economy with a significant amount of redistribution from the wealthy to the poor and some business regulations for prosocial reasons. 

b. A command economy where a centralized government has control over (or attempts to control) almost all aspects of the economy. 

In my view, the former may very well be the ideal for developed countries at the moment but I am rather skeptical of the latter. 

A point each in addition on the pro/con side.

Pro: If a non-EA fills a position and can do the function just as well with less alignment, this frees up the EA for a higher EV use of time. The non-EA, not being as concerned about EV, would, on average, choose a less impactful position, because impact is not as high of a concern.

Con: EA positions carry connections, influence, credibility, and other social capital that can allow for impact beyond one's direct job duties. To one who is concerned simply with doing their job duties competently, there may be less incentive to otherwise responsibly use their "insider" position to better the world.  

I messaged you. Good for you for looking to make a difference and develop your knowledge/skills.