I dont think you need to start with the prop. Its just going to take that much longer for the long acting test to kick in and prop can be quite painful, especailly for someone that never used AAS before.  Plus you dont really need this many compounds. Test and the dbol to kick start would really be all you needed. 

The longer you can wait between cycles, the better. After PCT is over for the first one, you will just be able to begin recovery. You really are not recovering much during PCT. Its after you are off of it that you will see the difference. So really, your best bet would be to keep teh cycle at 16 wks and rif it right into the show othereise, the short break isnt going to allow you much recovery. Not to mention, the second cycle's effect will be greatly reduced since it would pretty much be a continuation. So that being said, you might want to think about starting the cycle lighter, then building at you go, adding in a hardnener toward the end. and possibly adding in fat burners.  The guys I'm working with for fall shows alrady finished their off season cycles and are taking a break before we start the diet.