The problem with books is that most people learn by doing, and toy problems don't teach you what a real application is like.
I'd suggest picking an open-source project and doing something with it. Depending upon the type of programming you want to do, add something to Linux, OpenOffice, or any of the number of Java-based things. (I'm currently working with the Sakai course management system. There are plenty of things that need doing there.)
The languages aren't any worse than what you're used to. The problem is that real programming these days tends to involve lots of complex libraries and frameworks. Those are hard to learn in the abstract, which is the reason for my advice.
Whether it make sense for someone to (re)enter programming as a job I can't say. That's a decision for you. There are a lot of problems with the profession. But there's also lots of important things that need to be done, and a lot of the people who think they're programmers aren't up to it. Programming approaches are changing often enough that skills go out of date in a few years. That's both good news and bad news for people like you. Since people have to learn new techniques all the time anyway, it's not like you have to relive the whole last 30 years.
The language depends upon what you want to do. Systems software and desktop applications typically use C-based stuff (C++ is probably the best place to start, although Objective C and other things have advantages.) Web applications use Java or .NET. I'd probably start with Java. You can find real and interesting applications in just about any language, so you can argue for Python, Ruby, and all sorts of other stuff. But C++ and Java are probably the place to start. I keep hoping that there will be some major new programming technology to use multiple processors / cores well. But there are lots of nice demos, but so far I haven't seen an approach that looks like it's going to really take off. That's really pretty discouraging. I wish things were more different from when you were programming. C++ and Java are only slight improvements on what you're used to. It's really the libraries and frameworks that are new.
If you're thinking of web-based work, I strongly suggest learning Javascript and at least one major Javascript programming environment (e.g. jquery or one of its competitors). UIs are increasingly moving into Javascript.