I am planning my wedding...?

and it was originally for sept 17th BUT i checked all the places surrounding us that i could find or think of & that i liked & everyone is booked. Well my fiance wants it in may, september, or the very beginning of october. Well its hard to do it just any weekend in the month because he works on a rig & the places we absolutely love are booked on the days in september he could do it. & oct 1st is open but were thinking maybe may 14th or 28th do yall think i could get it all planned by then stress free? Also anything yall can tell me i need to help? Like i know invitations, flowers, all kinds of stuff but tell me everything you need to be planned by then because im not sure of everything lol..