27 Spider… I salute your persistence.
Sounds like you need the special order Extension Sleeve which is the sheath only version of the Stealth Regular with ball band. This would eliminate at least half of your issues you describe.
I would need to know your girth measurement at the base, mid shaft and behind the glans to ensure you have the proper fit the entire shaft length to eliminate most if not all the other problems as well.
You can contact support at the email@example.com email for making arrangements to shop you out the custom Extension Sleeve free of charge.