As far as I know,  60 days grace period after completing your OPT is the time during which you are supposed to pack your bags and get ready to leave the country. You're still in legal status then. So if you want to maintain status then you should either start college or change into a different visa type within that time. I don't think it matters whether there was a gap between graduation and OPT start date. You should still be able to get 60 days grace in the end. If you're worried that your H1 status might not work out you should check out colleges and start applying (just to be on the safe side). Another possibility would also be to enroll in short term programs like ESL courses by Kaplan to maintain your status till you can find another option.Your best source of advice would be your international student advisor at your college that you graduated from. So you should seek him/her for help.