I would more certainly go with plan 1. You don't want to start injecting with prop. It can be a very painful experience, injecting prop into virgin muscle. It can be rough for seasoned vets. Test e is a much better option. Plus, It's the long esters that are great at building muscle, IME. You can control estrogen conversion with an AI, but I would limit it's use. Too much AI will effect your gains.
For HCG, I suggest 250iu 2x wk through the cycle, then cut it off at least a few days BEFORE PCT starts. HCG will hinder your ability to recover as long as you are still on it in PCT.
Getting everything ready before the first pin is a great idea. I've seen it too often that guys start a cycle with half their gear and then when something goes wrong, they are screwed. They don't have protection from estrogen, or they run out of test after 5 wks. It can be a mess...and can totally be avoided. Good call ;)