Trying to choose between these two:
http://www.sanroccay.com/charterboat_dana_j.html
Dana J - 39 ft commercial marine
and

http://www.sanroccay.com/charterboat_summer_hunter.html
Summer Hunter - 39 ft sport

We have 6 guys and will be doing more trolling. The Dana J looked a little more roomy, because the space in the rear of the summer hunter seemed kind of small for 6 guys and 5 hours.

Does the boat matter?

Not as much as having a captain that puts you on fish. I can handle an iffy fishing boat setup wise if we're catching fish a lot better than having a perfect boat layout and not catch fish due to the captain not applying the right skills, techniques, and not fishing the best locations.

IMO, the Dana J is set up for drift/bottom fishing, the summer hunter is set up more for trolling. Not sure how many lines would be deployed, but I'd guess 4, maybe 6 with the outriggers they've got. Taking turns on strikes is common with trolling trips.

Folks with more trolling experience might chime in on the chances of getting all six fishermen hooked up at once while trolling.
IMHO, if your going to troll all else being equal go with the Sportfisher.

Of those 2 boats I'd choose the Summer Hunter.

bcfisher, are these 2 your only options ?? how far offshore you headin ?? what ya tryin to catch ?? and more importantly what have the charter guys been catchin ?? bear in mind a 39' can get small really quick with 8 people on it, especially if it gets a little sporty out there !!

Does the boat matter? [/quote]

its the only thing between you and the bottom of the gulf, it would matter to me !! jmo

Not going bottom fishing, just trolling. I don't expect we are going to far out on a 5hr. The boat does matter yes, but for catching fish does it? The dana J looks more like a bottom fishing boat where you could have 8 - 10 fishing all around it.

offshore trollin boats are equipped with outriggers, neither of these boats appear to have them. you cannot make a very good presentation of the baits without riggers. i personally wouldnt spend the money for a trollin trip on a boat thats not rigged for trollin !! these boats look fine for chunkin or bottom fishin, trollin no thanks !! jmo

5 hours is not enough time for a offshore trip.