this truck will be used all 4 seasons, and it will definitely see snow including the potential for a sudden 12 inches overnight
So stay close to stock, keep the rear duals, not super single conversion, and buy tire chains.
Whatever changes you make be sure you can easily put the chains on.
A lot of the choices you list involve massive unsprung weight increases which equal rougher riding.
For the travel you do, in Ontario, 4WD is not a neccessity. Chained up duals will be more effective.
The 19.5 rim is for low profile tires. Jumping up to 22.5 or 24...... will definitely need a regear.... will they even fit? They will be wider, they will be WAYY taller.... And they will be much heavier. 22.5 and 24 tires are built for TRUCKS, not ambulances.
Stepping down to 17 or 18 will let you go to a taller profile and keep the same basic tire height IF the brakes will allow smaller rims.
If the rims fit over the brakes, 17" will give you a massive tire selection and likely more economical if they have the correct load rating.
You need to talk to your local tire shop and find the tire you want first.