The hull can be transported as you describe, by putting some cushioning between the trailer crossbar and the hull and then just strapping the hull down securely.
This looks like a fairly old hull, so the expense of having someone do the repair may not really be worth it, but if you don't want to tackle the project yourself, that may be the only option. If you're not really concerned about cosmetics, you may be able to see if the repair guy can drop his price a little for a less than "perfect" repair. What I mean by that is that a large amount of the time required for fiberglass repairs is due to the sanding, fairing, blending, gelcoating steps (the processes that make the repair "invisible"). If you bypass those steps, will still end up with a totally structurally sound repair that just doesn't really look too nice but is fine to sail. This would take a fraction of the time to complete as compared to a repair that is perfect and undetectable.
Another option would be to find other Hobie sailors in your area (a Hobie Fleet) and see if anyone there could help you out. Most Hobie sailors would be willing to help you with this project for the cost of materials and a case of beer.
If you want to tackle the project yourself, it's also not a bad option again if you're not overly concerned with cosmetics. Achieving a structurally sound repair is not too difficult, but getting it to look perfect is really the challenging part. To repair this damage properly, you would have to do some grinding on the hull go remove the damaged gelcoat and really see the extent of the damage. You would almost certainly need to laminate fiberglass cloth. Don't be tempted to go the route of just smearing putty (Marine Tex) into the cracks. It won't hold up and could allow the damage to get worse. If you're not comfortable tackling this repair, then for sure bring the boat to someone who is experienced.
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