I've been thinking about a Ford Transit van, Guy Martin style, but now I'm thinking about a trailer. Stealth Trailers make an aluminium bike trailer that is pretty awesome. It weighs about 1200lbs and carries another 1700lbs, so something with a three thousand pound towing capacity would manage it. Fortunately, the Jeep Cherokee I'm currently fixated on can tow 4500lbs.
Track Bike (newer)
Kawasaki ZX-6R if I wanted to keep it Kawi as I have thus far.
Other short listed bikes would be the Honda CBR600RR or the Triumph Daytona 675R. All three are mid-displacement bikes that would allow for an engrossing track experience. A litre bike is a bit much for track day riding, unless you're either an ex-professional or compensating for something.
Price range (new) : $12,500 (Honda) to $14,500 (Triumph) with the Kawi in between. I'd pick the one that fits best. Rather than a new one I'd probably find a used one and then strip it down to race. I could find a lightly used one of these for about six grand and spend another four to get it race ready.
Track Training & Track Days
Racer5: The three day intro-weekend would do the trick giving me the basics on a rented Honda.
Getting in some laps at Grand Bend...
$100 a pop x 5 a summer = $500
Pro6 Cycle track days at Calabogie
$350 a pop x3 a summer (x2 meet up with Jason) = $2100
Join the VRRA and take their racing school.
A mid-80s Honda Interceptor would be my classic bike of choice. I couldn't care less how competitive it might be, this is an exercise in nostalgia.
You can find well kept ones for a couple of thousand dollars online. Converting it to a race bike would cost that much again.
Road racing ain't cheap...
~$18,000 + race costs (tires, etc)
OFF ROADSuzuki DR-Z400S x2
Build out a couple of Suzukis, do some training, complete some multi-day enduro events.
~$7000 each + maintenance and upgrades
Trail Tours Dual Sport Training
Smart Adventures All Day Training
$2000 competition budget
Forty-two, eighteen and sixteen and a half thousand (~$76k) and I'd be having a very busy summer expanding my motorbiking repertoire both on and off road. That's only a two thirds of the price of a new Range Rover! What a deal!