Yes, it works! At least for me.
This year I use up my OPT on May, 15. The new 2005 H1-B begin to accept application from May, 12. I use 2 weeks vacation and one week leave without pay until I get the H1-B Visa at the beginning of June. Absolutely no problem. Of coure, it depends on your company. Company will decide to accept this case or not. You can work first and if you work very well I think company will help you.