Thank you for taking the time to leave feedback. I mistakenly assumed that a player would always be coming from the closest checkpoint when fighting the boss. Like you suggest, an extra checkpoint before the boss would fix this. I'll keep this in mind as I design the open world segments going forward.
As for your recordings and any additional comments you have, I would greatly appreciate it if you shared, if it's not too much of a hassle for you. No such thing as too much feedback.