The Jordan King episode brings to mind just how many times he was so close, but ended up missing out.

The time he was robbed at gunpoint of 5 grand, which he was going to put on a hot stock;

When he got greedy with the mob boss' daughter, though he actually declined the money just wanting to get out with his life;

Phil didn't leave him all that inheritance money;

Dan did dump a couple women with rich daddies I think, I know at least in the finale he did;

Any others?

You could also include the time when he had built that amazing stock portfolio, but lost it all to an IRS audit.

Good question. Poor guy lost out more times then I can remember.