Texas to Central Am/Caribbean
To begin with I have never been that impressed with the Elites both from a build quaility and sailing characteristics standpoint. While Elites have some nice features my actual experiences with these boats suggest to me that they are in the same build quality range as a Hunter, Catalina or Beneteau, but selling (in good shape)at substanially higher prices. As to sailing abilities, these are very beamy boats with a lot of flair to their topsides and a fairly blunt bow. Sailed reasonably level and in flat water they sail reasonably well but are very hard to sail well and comfortably in a stiff breeze and a chop. I found that in gusty conditions, especially when combined with a steep chop this boat has a propensity to suddenly round up more agressively than almost any other boat that I have sailed in the past 10 years. This would not exactly make this an ideal boat for this kind of trip.
Because of this boats hull form, I would suggest that this is a very poor choice to convert to an outboard. The shape of the hull is such that it would tend to ''jack'' the transom out of the water and so in any real breeze you could not run the engine while sailing. There are times when you are cruising that you need to run the engine to recharge the batteries in order to run the running lights or autopilot (these boats are not a good choice for a windvane because of thier sailing characteristics).
I assume that you are looking at the Elite 30 in Kemah Tx. I do not understand why it is priced $25,000 below its market value. If you do move ahead with the Elite, you will need to have it surveyed because there may be more problems with this boat than meets the eye.
Assuming that you did buy the boat to go cruising, I would figure that you will probably end up putting $10-15000 beyond the purchase price into the boat to get her ready. You can expect to replace at least the mainsail (it looks original and poorly treated) and add a 80 to 90% jib for heavier conditions. You will need to add additional battery capacity and charging capacity, you will need to add additional fuel capacity (especially if you go to an outboard). If you go to an outboard you will need to add bilge blowers, and swap out all of the switches and electrical components for explosion proof components. You will need to add proper ground tackle and handling gear. You can expect to change out a lot of little things such as the plexiglas portlights and plastic sheave blocks which at 18 years old in the Texas sun are probably at the end of their useful lifespan.
While this may not be an ideal boat for your venture it seems like a bargain if it is in solid shape (something that I am skeptical of). Good luck whatever you decide to do here.