You raise an interesting point on readability. Languages always seem to start with ease of use and straigtforward readability as the dominant forces, and then move to power over time, but perhaps the languages never really target simplicity at the beginning; simplicity happens at first because of a lack of time to add all the features in v1.0.
There is a great way for Microsoft to address this concern in .Net. Maybe they are taking advantage of it.
There do not seem to be immediate plans to add generics to VB.Net. Looking at the only slight differences between the two languages one would have to conclude that either Microsoft introduced both of them simply to make migration slightly easier for people with different syntax affinities (sort of liking having multiple color M&Ms, just because some people prefer red), in which case the logical course would be to eventually merge them (into something like cb.net) just so people would stop asking what the differences are (given that languages are NOT like a bowl of M&Ms) -- or, conversely, that they introduced both of them in the expectation that the two would diverge somewhat over time (consistent with some of the earliest positioning by Microsoft of the two langauges).
In other words, maybe the answer is that VB programers, who probably would have been willing to learn C++ if it weren't for templates, would use VB.Net, keeping them safe from generics, and C# programmers, many of whom came from C++ and won't be happy until they have something like templates, will embrace them in C#. Microsoft would keep VB.Net simple, and make C# more powerful.
It is impossible to know where Redmond will take things (they could surprise me and announce generics for VB.Net tomorrow) but letting the languages diverge a little more certainly would address the concern you raised, while providing people who are willing to traverse the learning curve access to the facilities they want. This would give the two languages more of a reason to coexist, and would be consistent with that differences that exist in the two languages today.