Is it too difficult to plan for FG "vacations"?
Well, for winter, early spring and fall trips, the odds of a trips "going off" can be quite low. Some winter seasons, not a single trip makes it out. I would not recommend someone plan a trip for the "rough" seasons unless a) their travel time is short b)they are highly flexible and can reschedule.
During the winter, I will book more than one trip, just to increase my odds of making it out. I told Rick the other day that I've only made 2 winter shark trips, after many years of "trying".
Mid to late Summer trips are a little easier and, with a little care, can be planned for the traveling diver. I have met divers from as far away as California who have dived the Gardens. I don't know how flexible their schedules might have been if the trip was unexpectedly canceled, but they told me they came specifically for the diving here.
With a late June to August trip, I will still recommend you buy "changeable" airline tickets and be amenable to sudden changes in your travel plans. I would also suggest you book more than one trip. If the first one "goes", give yourself enough time to find someone to take your place on the second (or simply GO TWICE). If the first one blows out, you still have a good chance of making the second.
I would schedule my arrival for as late as possible on boat departure day, so as to give you time to check before leaving home as to whether or not the trip will go off as planned.
Check the weather, starting the week before departure. In mid to late summer (before September), tropical depressions don't usually form unexpectedly in the the Gulf (oh, but the do, anyway on occasion!) This information will give you a little heads up and prevent any surprises. You can also log onto the NOAA bouy site, which will give you sea conditions all around the area, including those right at the Marine Sanctuaries.
On the day of departure, you should check the bouys and the weather for the Gulf. Around 1pm, or a bit later, you should call the shop or club that booked your trip (at least that was what they used to ask that you do). The trip coordinator will have contacted the dive operator by that time and will have the "GO" or "NO GO" in hand.
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You can still show up to find the trip canceled, or you can even go offshore, only to turn back, but such occasions are rare in the summer. If I lived somewhere that required I fly in, I would be tempted to piggyback this trip with a more predictible one to Cozumel. Show up, dive the Gardens, offgas for a day or so, then head south. If the trip cancels, try to arrange it so that you can arrive either arrive early in Cozumel or do a little visiting in Houston (the Space Center, Moody Gardens, or the any of the big Museums would be nice).
I would, however suggest you have some sort of backup plan.
