The general idea heading into the last few weeks is to manage delta while waiting for theta to kick in. This is a potentially dangerous game to play (rolling in with <30 days) and might require a little more attention from risk management standpoint. To answer some of your questions:
1. Yes, it’s too expensive to roll at this point, that’s why we’re doing No.5 (incase we’re forced to roll if short strike gets close to ATM)
2. Taking off spreads also removes short gamma, otherwise we’d have to pay up for long gamma in OTM options and then face the risk of getting hit by theta.
3. If new spreads that were sold start to backfire and they double in price, I’d consider buying them back and leaving the rest of the trade on.
4. I want to be out of these trades the week of expiration or earlier (if possible). And remember, we’re not going to keep ALL of the premiums on either side of any IC.
5. See No.1