As Richard mentions, lots of obstacles in the Gulf. *The other problem is that the shallow waters can make the going very uncomfortable even when winds are not particularly fierce. *Direction of the wind is important. *The Gulf can be pretty uncomfortable in 25 knots regardless of its direction.
Are you familiar with GRIB files? *For getting a handle on weather, these visual files are an excellent adjunct to the weather forecasts you can obtain from Weather Underground or NOAA. *I heartily endorse downloading GRIB files before setting out, they will provide you with a visual reference to the forecasts you hear on your VHF weather channel, and will cover a greater area than your local weather reports.
You can read more about them, and download the Ugrib program HERE
I recommend that if you are not familiar with it that you download it every day for a week or so before you expect to leave so you can compare what you see with what you are getting in terms of weather and weather reports. *The very slow departure of winter from where we are now had me downloading GRIB files, as well as checking Weather Underground, on a daily basis, and the daily changes in 3-day and 5-day forecasts was surprising. *No wonder everybody was so unhappy with the televised weather reports.
Peter and I have had to go with sometimes one- or two-day weather windows. *With our nimble power cat that we can sometimes push to 16 knots, yet we like to have "bail out" options along the way. *You can't do that when crossing large bodies of water, and then you need to look at the overall pattern of weather to give yourself the best possible conditions. *For us in a sailboat, that meant the very best weather window possible until we were well offshore and away from those things that go "bump". *Destinations aren't so critical since it's not so terrible to just heave to offshore until the weather calms enough to make landfall. *Try to remember that nothing is so critical that you have to risk damage or injury in order to get in "on time."
Remember to ask as many questions as you need to feel comfortable with the answers. *There are no stupid questions.