Welcome..there is of course some risk involved in your plan. I was in this same place 10 years ago. I motored the boat down the river in November with a dirty prop and windy conditions to get it hauled for the winter the first year I owned it. We survived, but, in hindsight, I am surprised the motor ever got us there, but they are robust...despite our, or the PO's, neglect.
The water leaks are a little concerning, and thankfully, the very concerning gas leaks seem to be (temporarily??) solved. Any smell of gas is very bad, but the water leaks can maybe be remedied with the boat closer to home and time to diagnose them better. Mine looked pretty bad on the outside too, and she is still running 10 years later.
Make sure the bilge pump works!
