Renting a car is not so hard.
Driving effortlessly depends. Assuming you're Canadian, you are used to driving on the opposite side of the road than in Japan. That's the first thing to overcome, including being able to shift gears with your other hand.
Second, it all depends on how much Japanese is on the road signs. The more rural you get, the less likely there will be English. Can't say what the situation is with rental car navigation systems and English.
Taki is about 60 km from Toba, so figure at least an hour just to get there. (Google Maps will show the way.) But you can get there in less time than that for only 700 yen each if you take trains. See Hyperdia.com for how.
How are you going to locate the city office, let alone search records, if you can't read Japanese? And 1904 is quite a long time ago, so do you have any idea whether any relatives, let alone the farm, are even still there?