Hi Rook and welcome to the forum. The Odessy is very similar to the Oasis but without the Mirage drives. We really like the Oasis it has geat versatility!
For loading, here are a couple of relatively inexpensive ideas that may help:
If you have a hitch, you can get a t-bar like this:
Or save even more using a less expensive bed extender in a rotated position like this:
Note the boat should ride upside down on its "rails" unless you have a rack and saddle system. (You can load it upright and flip it if you need to). The bottom is thinner and will dent if left on your rack for any appreciable amount of time!)
Or you can make a rack extender like this (no hitch necessary):
Using a larger tube over a smaller makes a dandy roller:
Load one end at a time for easier lifting. Note use of towels or carpets for no scratches.
If you have a rudder that is in the way, you can load the boat backward to keep the rudder off the ground.
Hope that helps!
For some of your other questions you can use the "search" feature on the forum for ideas. There is no lack of info there. Or maybe someone else will chime in!