pick a reputable marine hauler and the boat support issue should be a mute point, however some haulers will have you sign a waver for damages on a boat of this age. this shouldn't be an issue if the boat is as solid as you state. also they will probably have to remove the flybridge(if equipped) to transport the boat. as to the seal question i assume you mean the shaft packings and i would say yes, now would probably be a good time while it is out of the water, and while this isn't very difficult you may want to have someone withyou who has done this before to show you how to do it properly(or hire someone to do it). While it is out pressure wash the bottom ceck the rudder and shaft zincs(if equipped)and if time permits repaint the bottom with a good grade of bottom paint, this will keep you from having to pull it for at least 3 to 4 years unless youstrike something and ding a prop.

P.S. while it is out record your prop size if you don't have spares incase you should need to order new ones, or find a deal on a spare set on E-Bay or at an auction.