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Actually rereading the series right now for nostalgia purposes...
I've only read one - The Return of the Great Brain, which I like and enjoy re-reading every now and then.
I don't know if I really relate to it. It's interesting that it's narrated from JD's POV; JD not really being the main character. Kind of like Watson narrating Sherlock Holmes mysteries. JD is more relatable than TD (I'm pretty sure they all have the same middle name, feel free to correct me) in that he's not super-smart and often does things he regrets. However, in The Return of the Great Brain, he often seems to goad TD back into swindling, which I think is particularly unwise. According to the back of the book, it's because he doesn't really believe TD has reformed, but when you think about it, wouldn't it be better to try to goad him to sticking to his reform? JD seems to be playing the little shoulder-devil instead of the little shoulder-angel. I think it's near the end of the book that he admits that he misses the old TD, even though the old TD used to swindle him.