Original Poster says he'll be using the tractor a lot. There's a lot of variation in 'lot'.
Lifting those fuel cans will become less inviting after about the fourth time or so. And slopping diesel around the filler spout and over the hood and engine will make a mess that will accumulate oil-caked dust and reduce engine cooling. To fuel mine with a can I have to use a stepladder. Did I mention falling with a can of diesel landing on your chest?
Look on your local used market (garage sales, estate auctions, contractor auctions) or even Tractor Supply or Atwoods for new and find a steel tank and pump unit. CraigsList (caution for scammers) and maybe eBay are good if you shop carefully. Harbor Freight, Northern, your local cheap discount tool house.
I picked up another 55-gal white square steel tank couple months ago for a hundred bucks (garage sale, moving, everything goes) and had the electric dispensing pump included. A HUGE savings over new. I've seen 96-gal "L" toolbox tanks go by occasionally too. You just have to keep looking.
You can use the tractor to set the smaller 55-gal tank into your truck and run it to town to get fueled. Add stabilizer and you're good for six months or so.
Pull the tractor up to the tank (set on a pallet), clip the pump motor leads to the tractor battery, and pump away like you own a gas station.
A handy accessory is an automatic shut-off dispenser nozzle; again just like a gas station. Prevents overfilling and run-overs.
Don't forget to add a filter too: either a screw canister type (think oil filter) or a sediment bowl type. I use both and have a second canister attached right at the nozzle to keep hose deterioration debris out of the machine tank. Cheap insurance.
Before you fill your tank the first time, plumb a 1/4-in brass valve in the bottom side outlet so you can drain water off before every fill. Use a plug in the valve to prevent accidental opening the valve and spillage.
In your area there seem to be two brands of pump: GPI (silver) and FillRite (red). I've had commercial users tell me the GPI don't last.
If you don't want an electric pump to start off (building your setup in increments) you can use a steel tank with a manual hand pump. I'd go with rotary or diaphragm rated for diesel (although less common, you can find these used and worst case rebuild them). I've tried a $20 'water pump up- down handle' type barrel pump and found the packing at the rod port under the handle leaks no matter what I do.
Having a fuel dispensing station will make your life easier and save your back.
Please post back your experiences so we may all learn.