That trade manager software looks really cool. Itâs a good idea at least. Iâm not sure that it can ever match some of the commercial software out there though. I guess only time will tell.
I've never used Ruby or R either, but as a former VB programmer I'd second the notion of learning C#. It really is a good language to use and you can do a ton with it without getting into the complexities of C++ or C. Plus Microsoft has thrown its full weight behind it which isn't a bad thing.
By the way VB and C# are almost identical (except syntax) so you can stay with VB which gives you measurable productivity gain over C#.
I'd pick either C++ or C#. And you can take a community college class and learn almost everything you need in a few courses. Keep trying to code your strategies on the side and bug the teacher for help with your code.