The ideas you mention is certainly intriguing: a guy who gives himself everything and then things go wrong. I have to say, though, as a reader I prefer to either like my protagonists or at least be in awe of them if they’re anti-heroes, so annoying brainless teens isn’t usually my cup of tea.
And perhaps making the ending of book 1 a cliffhanger isn’t the best idea. Making a living is certainly something all writers aspire towards, but the end of a book is meant to be the end of a book, regardless of its place in a series. If you end on a cliffhanger it’s just you telling the reader they’ve been fooled into buying an incomplete book, and I find that…immoral o.O
Having said that, though, a few of my favourite contemporary YA fictions did that and I’ve been suckered into getting the subsequent books. I still don’t condone doing it, though!