I just went through the same debate......and read alot on this forum about it...
My only caveat here is that I've not been out in a gulfie...but from everything I hear, they are awesome.
There are alot of threads on the pros-cons. The Gulfie, IMHO, is the most boat for the length.....bigger fishing cockpit (no euro transom), more beam.....which converts to better riding. But alot of guys say you really need twins to make the boat handle better....not sure about that...there are a few guys here who have a Gulfie w/ a 250 and are plenty happy. If I had one though, I'd buy with twin 150's.....or if a single, the new 300.....I think that boat would be a little underpowered with a 250, loaded with fuel, gear and your fishing buddies.
If you're trailering alot, the Journey is the way to go - its 8' 6" beam is legal to tow in most if not all states. It not a big deal though, depending on where you are and how far you tow - for example, I see a few gulfies towed around my area across town to the ramp and the cops never care....doubt they even know its bigger than 8' 6". But if you're trailering long distance, the troopers/highway patrol will know....
I like the traditional v-berth setup of the journey vs. the bunk setup of the gulfstream. That is because my wife, small child and I can all fit in the v-berth. The bunk on the gulfstream is small, and if a kid is sleeping there, hopefully he doesn't roll around alot!
The cuddy in the gulfstream is nicer though for hanging out...as you almost have a couch setup with a galley on the port side of the v-berth. Could easily sleep one dewd or a guy and his wife/girlfriend....but its a bit close for 2 fishing buddies unless you are a true fan of brokeback mountain.
There....there's my "newbie" -- never rode in a Gulfstream but read alot about it cause I was making the same decision, analysis.
Good luck!