This is just my opinion, but even if the local hobie dealer is a few hrs drive away, it would be worth buying thru them. You pay the same price for Hobie Kayaks wherever you buy them from, and the dealers are the front line for after purchase support and will typically go to bat for you if you have any problems of any kind. I know the Hobie dealer I go to (Economy Tackle in Sarasota Florida) really goes out of their way to support the product. One example, the weld broke on my scupper cart recently, instead of having to mail the cart somewhere for evaluation and exchange (which could have taken weeks), they just took my old cart and gave me a new one. They even mounted the wheels on it and made sure everything was working correctly.
I don't know if every dealer does this but since I bought my kayak from them, I get a 10% discount on any accessories. You will likely need PFD's anchors, scupper carts, rod holders, etc, etc, etc. once you establish a relationship with them and they know you by name, they are just a phone call away for any questions or problems to give you expert advise. Another example I can give is on one of our older kayaks the rudder lines came loose, I called them and they described exactly what I needed to do to adjust them, I was able to fix it my self with their excellent instructions, they concluded the call with hey if you can't get it to work or have any problems just bring it down, we'll fix for you, I've taken a couple of the boats in for little things, and they always fix me right up. Even if they are not close by building a relationship is good in my opinion. Another big deal for us was when we got our first Hobies, we purchased the roof racks from them as well, they installed the roof racks, insured the kayaks were secure for our drive down to our other house in Key West which is a 300 mile drive, we directly left from their shop for our trip (we've actually done that about 4 times now ( we've owned 7 or 8 Hobies now over the years).
I'm sure they could work out a drop shipment directly to your house, but it were me, I would just take a drive down there when it arrives, have them set it all up and assemble everything for you, they will assist you in assuring that you have a safe carrying system, and you can pick up all the needed accessories ( hint:::: Hobie Kayak sail kit, and sailing rudder) all at the same time. You will be ready for the water.
You can do what you like, that's just what I recommend, since everything Hobie related is done thru their dealer network. I know from my own experience if you just call any random dealer demanding resolution to some problem, if they don't know you, and you have never bought anything from them, I just don't see them jumping thru hoops for you.
If you ever want to put a trolling motor on, even if none is planned right now, I would ask for the MCO (manufacturers certificate of origin) document. This is a legal document that must be presented for any registration, licensing, and most insurance carriers require them. You can only get this document from the dealer who sold you the boat, Hobie or anyone else for that matter cannot send it to you, it has to be from the dealer who you buy the boat from (no exceptions, for legal reasons). I foresee in the near future even kayaks with sail kits will need to be registered (some states are beginning to do this already), it's best to be prepared.
I license and register all my Hobies so if they ever get lost or stolen, you have a means of getting it back if recovered. Were not talking a $200 dollar kayak from walmart here, these things are very valuable and will last you for many years.
Hope this helps