I did it once, in Aug 1992. At that time of year, once you are beyond the sea-breeze zone of the coast, the place is one great un-nerving calm with thunderstorms everywhere, and a very, very light breeze from 120 deg.... right on the nose. If so, virtually all your progress will be on the prop so budget for the entire distance on the prop, so that will mean a lot of fuel storage, and carry lots and lots of engine and gearbox oil!!! Been there, learned that!
Take your motor for a long, long run first and watch every oil seal and temperature guage.
I cannot speak for any other time of year, but I understand that there is some wind in winter? I smile.
Be careful leaving Houston. There are many oil rigs about, and you will have to avoid them. We were blessed with good visibility until we were free of them, but it may not always be so easy to see.