Yikes. I'd look at the i9S then or getting a valet
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Just speculating here as I've never done this, but you MAY be able to rig a strap-on kayak cart to the carry bag to facilitate wheeling things a little easier.
You can certainly bungee the bag, pump & cart in the stern of an i12S.
You should note that all that gear - seat, paddle, pump, mirage drive, PFD, sail, mast, cart, etc. is not going to fit in the bag. You could talk to your dealer about possibly getting a bag for the next larger boat (i.e. an i12S bag for an i9S). Otherwise you'll need to tote another bag along with you.
Good luck!