1. No, the pump won't fit in the forward hatch. I doubt the carry bag will either, but you probably don't want to take the bag with you. See the answer to Question 5 below. Most don't take the pump either unless they're going on a long, multi-day trip.
2. You can flutter kick the fins in shallow water. You push one leg forward so the fins are flat against the bottom of the boat & then move your legs with very short strokes. The fins will stay within a couple inches of the hull bottom but still provide a good amount of thrust, especially turbos. If you really prefer to paddle in those conditions you can flatten the fins to the hull bottom & use the bungee to keep them there while you paddle - no need to remove the drive. The fins are pretty tough & you can (usually) straighten bent masts on the water without a problem. The drive will still work with bent masts, or even one fin for that matter.
3. Yes, the Hobie seat is not good IMO. I would research getting a different seat. I adapted a Skwoosh high back seat which is taller & much stiffer than the Hobie seat with better lumbar support. Big improvement.
4. No idea about the sail. I don't sail.
5. Generally, you don't wheel the bag to the launch. You inflate & rig the boat at the car, put it on the cart & wheel it to the launch, same as a rotomold kayak. The bag & (usually) the pump stay in the car. The bag is not designed for long distance outdoor travel. You'll want to buy a cart, but see some of my other posts about balance issues with the Hobie cart...
Hope this helps!
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