Some things to get deeper into motorcycling in the next year:
Ford Transit Van:$53,472 + some more in accessories.
A means of moving bikes south in the winter to ride year round as well as a way to take off road or race ready bikes to interesting locations where I can exercise them.
The bonus would be to get all Guy Martin with it.
Become an off-road ninja:
Step 1: Get the kit: A KTM 690 Enduro, the best all round off-roader that can also get you there.
$11,999 + some soft panniers for travel.
Step 2: Get good at off-roading with lessons at SMART Adventures! $329
Step 3: Do some rallies like Rally Crush, Rally Connex, the Corduroy Enduro, the KTM Adventure Rally (in BC!)
Set up the KTM as an all year ride:
A Mototrax snow bike kit would let me turn the KTM into a year round steamroller. Back country riding in the cold months would make for some good exercise and training so I wouldn't be back on two wheels in the spring feeling rusty. $6000US
Become a road racing ninja:
Step 1: Build a race bike...
...but why be boring? Instead of something new take on a race bike rebuild! There is a '93 Yamaha FZR600 for sale nearby in need of some attention. They're only asking $700 for a fairingless bike, but that means I can go looking for race fairing! 
It turns out 90s FZR fairings are remarkably easy to source. Since this is going to be a race bike, I can go with a lightless race ready fairing. The other fairing parts are also available and not crazy expensive. Getting them all as unfinished moulds means I can start from scratch with a custom race paint theme.
I'd be spoiled for choice with classic race designs, but I think I'd do my own with a 90s style influence. With a double bubble screen and some customization of rearsets I could make a Fazer that fits me.
Step 2: (finally) take road race training:
Spend the weekend of May 11-13th next year at Racer5's introductory course at Grand Bend.Three days of track training on a rented bike. Later in the summer I could then follow up with the advanced courses on my own bike (the Yamaha would be ready by then). That'd be about two grand in race training over one summer. By the end of it all I'd have my race license and have a clear idea of how to proceed with a campaign, perhaps with the VRRA who also run a school. With the 90's FZR and the training I think I'd be ready to run in amateur classes.
Use next level tech to ride better:
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With those tools I'd be able to bike in ways I currently cannot. I'd have what I need to pursue both off road and more focused tarmac riding which would greatly enhance my on-road riding skills. If motorcycling is a life long learning experience, these things would be like going to motorbike university.
