If you dont care about resale on a 38' boat, the 5th will tow a lot better, have more clearance at the ramp, and will turn/maneuver much better in tight places.

A fifth wheel on that 38 will tow like a dream.

If you buy it and don't like it I'll trade you the bumper pull we have for a 38zx

I have a 40 Outlaw on a goose neck. It carries the boat pretty low and makes long road trips awesome. High crested steep ramps are no issue either provided your gooseneck has height adjustment built into the trailer at the ball allowing the trailer ground clearance to be increased by more than a foot. Also having the tongue weight over the rear wheels of the truck is safer imo.

Another excellent point. After thinking about it, what you wrote makes lots of sense. I'm going with a 5th wheel setup. There are too many towing advantages to do otherwise. Thank you!

If I could I would have a gooseneck trailer for my 30' boat. I like them more in every way. If I was shopping for a used boat, boats were the same, I would pick the one on the gooseneck trailer. That is just me.

Thanks for the input. I'm def going with a 5th wheel. Trailer is being built.

I am surprised the running length issue didn't come up. Many states here in the south east have length laws that have been implemented on towing. For boat or RV towing most of these southern states require a length permit over 65 feet long. http://towingworld.com/towinglaws.cfm This site has all the states listed so you can familiarize yourself with what I am saying.
My Formula 357 on a tri axle trailer makes my rig over 70 feet long which makes me need a length permit. A perfect solution to this is a gooseneck trailer and not only length but maneuverability. My trailer is a major pain to turn on the bumper compared to a gooseneck trailer.

You will do well with a gooseneck.

Great Point Aquaforce; I didn't even consider the length issue. My plan is to go with a 5th wheel for sure, and I'm using a short-bed dually to tow it all, so thinking I'll be within the limits. Nonetheless, I'm curious about what the length fees would be if I were over..

It's going to be close no matter what with that rig, unless it's a short bed regular cab ranger lol. My trailer is 52' prop nuts to coupler, add in a crew cab long bed and oops... Lol

Florida is mid to upper $20 range for an annual length permit which is not any money but a penalty for no permit will hit the pocket. The permits are not a huge deal just make sure you have them if needed.
The gooseneck will shorten things up a good bit since the hitch point is so far in and the boat can be so much closer. Some have gone to the gooseneck purely to avoid length laws. Some trailers have very long tongues and shortening them up can get under the length law but it is much easier to stay under the length with a gooseneck.