Blindly thinking that everything is fine is the fast way to be taken advantage of in many situations.
You are right to be cautious.
The reason everyone is saying "it will be fine," is because eleuthria has always
fixed these problems in the past.
In my opinion eleuthria runs a very tight ship (despite the problems) and has always put the miners first.
But again, one should always be cautious.
I also think he does a great job of keeping an open communication line with his members. This is not in any way trying to accuse him or anyone else operating a pool. What I'm saying is obviously more in general sense as you pointed out. The reason why I said repeating the same problem is something to look into is because problems should be fixed and not repeated. It is definitely a cause for me to be suspicious when I hear that same problems repeat over and over. It could certainly be legitimate each time, but repeats of such events should only lessen one's earned trust from others and not the other way around.
I'm always cautious to give my trust to people and there are plenty of incentive for people to befriend the subjects of their exploitation. There is a reason why "Keep your friends close and you enemies closer" is a common saying that everyone is familiar with. In fact, it may even be necessary for them be at certain level of trust to carry out their devious long term plans depending on it's design.
Caution should be practiced all the time imo, especially now. Everyone taking the proper precautions of their own can only help the community become more trustworthy by weeding out the bads through facts and evidence as proof.