Btw, if you're arriving in Osaka, you'd drive to Kyoto first before Tokyo (it's 1hr or so out of Osaka). I recommend a JTB Sunrise day tour, as they take you to some awesome culturally rich places. I was fortunate enough to go there during Cherry Blossom, but it was very busy.
 
Forgot to mention, tolls are expensive. so keep plenty of cash handy & make sure you goto the green sign lane (pay booth). From Tokyo, I drove to Mt Fuji, then to Lake Ashi & experienced the best winding roads (like straight from a game) in my life. Simply input the Mt Fuji tourist centre (phone number) into the gps, then followed the road to station 5. Afterwards, followed the main road in the direction of Hakone/Lake Ashi where I found plenty of excellent roads. 370Z would be awesome for that (unless Toyota 86 is available for rent by then).

Not just that. Sake is still in my blood.
 
For the record, the smokes were from vending machines, not duty free.....hehe

Honestly, a JR pass is a good investment (approx 30,000yen return or get a special for under 20,000 via a tour company - needs a bit of notice). I spent 15,000yen (near $200AU) in tolls in 2 days & I even avoided an expressway due to the twisties. At least 10,000yen each way from Osaka <-> Tokyo. Fuel & parking is also expensive too.
 
Bullet train is a fast trip anyway (smoke/eat/sleep). But then again, road trips are fun if you have a lot of time.
 
Drop off fees are approx 8,000-10,000yen ($100 AU+), sooo not worth it. I got pretty handy with the train system & found my way to pre-booked rental places without much drama (didn't even have a map or 3G access).
 
I ran the numbers too & split 3-ways, it was only fractionally cheaper to drive (compared to train). In retrospect, I'm glad I didn't drive to Kyoto. Bullet train was fun & I didn't waste time being tired & getting lost.

My suggestions/highlights:
 
- First issue I see is that Drift tours are on set dates from memory, so you may not have the luxury of picking a date @ your convenience. If you miss out, you can always make up by renting a nice car. 370Z would be great for the twisties, the R35 needs too much speed & the corners are very tight/slow for it to stretch enough.
 
- Buy a JR pass (prolly cheaper & much less stress).
 
- Take a day tour of Kyoto from Osaka (since it's so close - arrive via JR bullet train), then make your way to Tokyo in the evening. I don't recommend driving a car to tourist sites/spots as parking is an issue (will waste most of your time in Kyoto) & directions/navigation will be hard too.
 
- You can still get your shot at driving when you rent a car & goto Chiba. On that day or two, you can do the Mt Fuji/Lake Ashi drive. Depending on where you stay, I'd just rent a car nearby (plenty around Tokyo & Shinjuku area). There's a Nissan car rental next to Shinjuku station (refer to tocoo site I linked above). Park at your hotel (I parked mine @ Keio Plaza in Shinjuku - where I stayed - convenient!).
 
- Go to both Disneylands.
 
- Scrub off the Toyota Plant. You probably don't have enough time & are better off spending it checking out Tokyo.
 
- For Tokyo, best view of Rainbow bridge is near Tokyo Teleport Station (Toyota Megaweb). Not impressive IMO. For when you check out Shinjuku @ night, scare yourself a bit & get harrassed by the Africans in Kabukicho (redlight district) & get intimidated by the Yakuza presence....lol Fish market is really dependant on if you're a food junkee. Tokyo Tower is a waste of time. Daikoku car park is annoying to get to (only by car IMO) & is really just ricey. After you see the cars in Chiba (Top Secret) & some of the surrounding VIP car dealerships, the kid in you should be smitten enough.
 
- If possible, befriend/pick up a local or two & they may show you an excellent time on the town.
 
- When you rent a car, go for longer than 6hrs. Traffic can be a bit unpredictable (better than Sydney though strangely). Use the opportunity to hit up some places in Tokyo late @ night, as trains stop @ midnight. There's some nice clubs that a bit out of the way by train/public transport.
 
- Near Mt Fuji tourist centre is a theme park (can't remember the name) with a CRAZY looking rollercoast. If it's open, GO!!! Additionally, I hear Edo Wonderland is good too (can catch bus/tour or maybe bullet train). I'm sure your hotel can help you arrange that.
 
- Specific Tokyo spots I recommend you prioritise are Harajuku, Shinjuku, Shibuya, Akihabara, theme park in Tokyo (another cool rollercoaster). Dont' really bother with the Imperial Palace or Shrines in Tokyo if you're going to Kyoto.
 
Above all....Drink plenty of SAKE!
 
Despite what people think, Japan is actually cheaper than Australia if you're smart. You can blow A LOT of money in Japan if you're silly though (like anywhere I guess). If/when you get lost & need directions, compliment the poor Jap you're asking about how nice their country is first (they're very proud). Everytime I did so, they were so helpful they would insist on taking me where I wanted to go.

Not sure sorry. I went on a Thursday from memory.

This is a bible!
I'm flying into Osaka, Kansai next month! from my motherland no doubt.
The Land of the Rising Sun is calling me...
can't wait :D

na/sdub 

We went to Japan for a snowboarding holiday last year and all my missus did was take pictures of vending machines. Hopefully you find something more interesting to photograph. 

LOL!
I bought a new decent camera for this trip so I'm sure I will :P
I was told I have "lots of courage" going there solo and not speaking Japanese...haha