Wow. Some of your questions can only be answered by you.
I've had 6 adults on my Getaway. It still performs ok, but obviously it's going to be slower than with 2 people. I was sailing (solo) with 2 friends with their Hobie 16s (they were also solo) in some high winds a month or so ago. In lighter winds, under about 15 knots, the 16s were faster than my Getaway. When the wind went above 20 knots, we were evenly matched...in fact, I might have been a bit faster since I caught up to them.
I think the dolly or beach wheels will take about the same amount of effort...actually, it looks to me like the dolly would take more work, but I've never used one. I have beach wheels, but have yet to use them on this boat. I did use them on a Hobie 17 I previously owned, and could handle the boat by myself on them. I would expect to set up the boat on the trailer, drag it from the trailer onto the beach wheels or dolly (which will probably take 2 people), roll it into the water and pull the dolly or wheels from under the boat. To recover, put the boat on the dolly/wheels while in shallow water, roll up to the trailer and drag onto the trailer. The Getaway is heavier than the 16.
The Getaway is about the same width as the 16, so if the Bravo fits under a 16, it should fit under the Getaway. The Getaway hulls are wider, and the crossbars may be lower, so if the Bravo is a tight fit under the 16, it MIGHT not fit under a Getaway.
Like shogun95 says, the Getaway has a built in righting line. Easy to right, as long as you are prepping it right...release the mainsheet and jib sheet, swim the mast around so the wind is coming across the front of the boat, and get one large or 2 people on the righting line. Don't get smacked in the head by the hulls!
Time to set up is dependent on what status you are starting from. I trailer my Getaway with the mast down (obviously), and rudders and float off. So for me to setup, I have to step the mast. If I'm alone, I need to use the Mast Stepper III which adds a good 10 minutes to setup, but if I have a partner, we just lift the mast. I have to put on the rudders, and the float, usually I put on my motor, and the other fiddly stuff...mainsheet, lower the wings, hook up the mainsail, rig the jib, etc, etc. So for comparison, when I first got the boat, I kept it on the trailer in a marina, mast up, rudders on, jib up and rigged (with a snorkel on the jib to protect it from sunlight). I had to put on the motor, rig the mainsail and back the trailer down the ramp. 10 minutes to rig and launch. Now, If I'm sailing with my wife (who knows how to rig the boat), we can raise the mast, rig everything and launch in 20 to 30 minutes. If you are sailing with someone not familiar with rigging it, and you have to direct everything they do, it'll take you 30 to 40 minutes. And, If I'm by myself and need to use the Mast Stepper, it takes me 50 to 60 minutes to rig and launch.
_________________ Yet another Bob! "Firefly" - 2012 Hobie Getaway with wings and spinnaker "Sparky" - 1978 Sunfish (OK, it's not a Hobie, but it's a fun little craft) Too many canoes and kayaks
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